Im kicking around the idea of getting rid of one of my cadillacs.....perhaps in favor of something a little later like a 66-70 convertible.
I have a 50 series 61 sedan that runs and drives but needs plenty of work. I do feel sentimentally attached because I had it at my wedding and its in a ton of photos.
Then I have my "dream" car a 56 coupe deville. That car has kicked my butt, needed everything and then some as I work my way through it piece by piece. I just got it running after owning it 9 months. It'll need a radiator, master cylinder and tires at minimum before I can test drive it.
Sometimes, I just want to drive. I want to cruise and not worry about stuff.
I kick around the idea of selling the 56 for roughly 6-7k and finding a convertible from 66-70 wich I'd like to hope would be a bit more of a competent driver. Doesnt need to be perfect, but I'd like to cruise down the highway with the top down.
Sometimes I look at my garage filled with 2 50's caddies and feel like a king, and lucky, and other times when life's beating on you a little, I go "what am I doing!? One drives OKAY around town and the other doesnt at all. Maybe I should just sell them both!"
I believe collectively I'd be able to scratch together maybe 12k which I think would buy a pretty good driver cadillac. But part of me knows I'll kick myself getting rid of my blue 50, with all the memories. I also wonder if I'd really miss the 50's styling when in a late 60's. Theyre 2 different beasts.
I never got attached to any vehicle, and I enjoyed almost all of them, but when it's time to move on and you feel the way you do, don't look back. There is maybe 1 or 2 cars out of all I've owned that I would entertain taking back. I find that variety is the spice of life, and your tastes change. Think of the quote "Nothing is Forever". I'll miss them until they leave, but then it gives you the opportunity to move up to maybe something that would involve less work, do a complete 180 because you feel like it was getting stale driving the same old vehicle, etc. This whole process is like a cleansing, and how would you find out if there's something out there that might better suit your tastes until you try it? Every car holds a place in my heart of an era passed and what I was doing, where I lived, and where my head was at in that specific time frame in my life. I never looked back, only moved on. For me the fun is working on them, not necessarily driving them. If you feel like you made a mistake, you can always purchase the same type of car back if you have seller's remorse. I just thinned out my own herd and sold approximately a dozen vehicles in the past few years. Wasn't even into driving those specific cars anymore, not even onto the trailer when they left. But a weight was lifted off my shoulder with that many less things to take care of, and the newly found freedom of choice to purchase something that fits my lifestyle and driving habits at the moment. But that's just my opinion. Good Luck with whatever decisions you make......
First of all, what a great problem to have.
I am the opposite of Bobby. I get too attached. But then I only have the 1.
I wouldn't mind something else but I just don't have the heart to sell my first and only. I have it insured for enough that if something did happen to it I would be ok, but I still baby it anyway.
As far as the original question, keep the one in your wedding ....... if you are still married to the same person that is. It may get your kids and grandkids into the hobby if they have old pictures of that car. Not to mention that your wife may object a little less if you have to spend $$ on the car that was in HER wedding-- you know, her wedding and you just happen to be there.
Can you possibly buy a convertible of that vintage for $12k that isn't another beater eating you up?
When the top goes down, the price goes (way) up.
I'm with Jeff, I get attached.
I've got a '70 convertible, bought about 2 years ago, have grand plans to take it on trips, though I am still sorting it out. It hasn't left me stranded or anything, but I'm leery. Brakes are good, engine is good, trans is good. Suspension is yet to be gone through, but currently there are no issues. With that said, all old cars (generally) need something.
The good thing about the "newer" cars ('66 - '70) is that parts are "somewhat" more readily available.
How about starting to look for that car you want, it will take time. If you find one, pull the trigger and get it. you can then sell one of the others.
Did I mention all old cars need something?
Best of luck on your decision, we only live one once (and for a fricken' short time) and you don't want to regret missed opportunities when they present themselves.
I appreciate your willingness to discuss your dilemma on the forum. I am sure there are others in the same boat, ... er car, ... er situation.
Your '50 and '56 are both lovely cars, but if they are far from a joy to drive (reliable, safe, comfortable), then you may want to re-assess where you stand in relation to them. I don't know the specifics of your cars, but if they are nearly original, there are many systems/components on '50s Cadillacs that are different from '66-'70 Cadillacs.
A '69 convertible has front disc brakes, a rugged engine and transmission, solid state AM/FM radio, and is not so old that a competent mechanic would have trouble understanding and working on it. Even though convertibles tend to be more expensive, I think you could find a decent driver in your price range. If it needed mechanical or body work, I think the work would be less expensive than work on a comparable '50s era Cadillac.
Your decision will probably not be easy, but take the time to make an honest assessment of where you are now, and where you want to be. If the projects you have now are losing their lustre, what's the point? I hear that at the next GN, therapy sessions will be scheduled :). Good luck.
People used to drive Cadillacs of the 1950's and newer in good repair across Country all the time. My Grandparents took my Mother from NJ to Pikes Peak in the late 1940's in their Cadillac.
I would spend the money to get those cars running strong and reliably, as it seems the money invested will be recovered if/when you sell them. Then you may not want to sell them. If you do sell them and opt for a newer RWD Cadillac convertible, the 1965-1970 drive more like a modern car. I drove my 1970 Cadillac today. Christopher is right. However, no modern mechanic is really able to work on them in the area of the Country where I reside. Have heard horror stories of timing chain (that was already replaced) being replaced in lieu of a $2.00 condenser on a 1972 Classic.
I appreciate the input guys.
The 1950 is a character of its own. Somebody, in its lifetime, bondo'd the rear quarter panel seams together where it runs down alongside the trunk. I never knew anything about cadillacs when I bought this car. I just saw it in person at 28 and it floored me. It had such presence to it. I traded the guy my 1998 mustang gt (my car since I was 18) straight up. It was dull and sun baked and wore out. To cheaply spruce up the looks, I did 2 coats of clear gloss lacquer, and, through amateur painting outside on a driveway last May, it achieved kind of this matte finish that I ended up loving. The exhaust leaks, will give you headaches unless you keep the windows down (I know, I know, dangerous), has a glorious burble, gets hot inside because I have bare metal floors from cutting out and welding in new patch panels I made from scratch. Doesnt like the highway the way its geared for whatever reason. Winds out kind of too high RPM wise for my liking so it stays on back roads. She left me stranded after a long cruise and stop at a grocery store the other night. Was too hot and was turning over really slowly. After 15 minutes with the hood up she fired up. 6 volt battery might be tired. It has its own character and history, and what I know inside is, if I sell it, I dont believe I'd ever buy another 1950 caddy. None of them would be this one.
The 56 needs all kinds of TLC. Rechrome work needed, floors, brake master, radiator, and who knows if the trans works. It just needs a lot of work. But it brings me joy everytime I open the garage door and see it in there, imagining what could be one day.... So close to a maiden voyage.
I'm learning a lot working on these two cads of mine. Just seems to me sometimes I see on craigslist these 66-70 cadillacs (convertibles and hardtops) in DECENT running shape for roughly what one of mine is worth, and its tempting. I suspected they'd drive a little more modernly as Scot mentioned. Right now my only frame of reference is my 6v manual everything 1950 caddy.
I guess I'm just anxious to drive. Arent we all
The word that best describes the way you're feeling right now is "Overwhelmed".....You're in good company my Friend. Happens to all of us, all the time. Goes with the territory..... ;)
Bobby B and Jeff's comments were spot on, even though they addressed the issue from different perspectives. Seems to me that you answered your own question though. You still have pride in ownership and both vehicles move you even though the '56 is still a project. Re-read your comments. Your personal pursuits must be your pleasure and it sounds like both of these currently remain so. It is when they cease to be pleasure, that the time to move on then occurs. It does not seem that you are "ready" to move on from either of these cars at the present time, so hang on to them for now and continue to learn and appreciate them. You will probably move on someday and these cars will have provided you with the experience needed to look after your next automotive beauty. Been there, done that, (also with a '56), and no regrets. I find they are either keepers OR prep work for the one that is meant to be. Clay/Lexi
I know what you mean to be attached. Each Cadillac that has left my garage gives me cause to shed a tear or two but sometimes we have to make the tough decisions. I currently have two Cadillacs from the 1950s and though they are beautiful cars and a great pleasure to drive and show, I find myself envious of those with cars that they can drive without great concerns. The idea of a convertible might be something that you want to think about twice. Having owned several convertibles, you really need to look at the amount of time that you would drive with top down. There is no greater feeling than cruising in a big Cadillac with the top down on a perfect day but how many of those do you get in your area. Driving with the top up on a convertible is noisy, and sometimes damp as they are prone to leak in the rain. In the heat of summer they are actually very uncomfortable, especially when not moving. As some earlier have mentioned "when the top goes down, the price goes up", so you might also consider a nice coupe. You still get the reliability of the newer Cadillac and also the sportiness of the coupe styling. You would probably be able to get a much nicer coupe for the same money as a convertible needing some TLC. Best of luck in this tough decision. - Greg
Your comment about getting stalled at the grocery store sounds like simple vapor lock. An electric fuel is the answer to that, not a new battery.
No, it was turning over much slower compared to when its cold
Rob, I understand your dilemma. I would rather drive than play mechanic but my tastes are for the unusual and being retired on a budget I need to fix them up to drive them. Restoration takes twice as long as we plan and costs twice as much as we planned on spending but the rewards are worth it in the end (If there is an end?)
Thanks for the input guys. Ive got some work coming up that'll put some more parts in the 56 so i can hopefully run it.
A few years ago, I sold a "Brand X" "heavyweight" that I had owned for twenty-nine  years! I didn't shed a tear, though was a wee sad. But two things happened after about 25 years of ownership:
1. Because of some career detours, I had come to realize that I was never going to be able to fully restore it; and
2. After one owns a car for 20 years, you discover, quite by surprise, that YOU have changed more than the car has!
(provided it's been stored inside) Peace.
For whatever its worth, I had my buddy come down to attend a car show with me. He brought his 2016 mustang GT 5 speed. Quite a good looking car. I had to drive it, as its been a few years since I drove a manual, and I used to own a mustang. Had a few spirited launches, but you cant use that much power where I live. Most roads are 35, some are 45, and theres always a healthy dose of traffic.
Anyhow, I have him drive my 50, as he's never driven anything that old. He was nervous and white knuckling it, getting acquainted with the bias plys and old worn out steering. Haha.
So in my neighborhood I take his mustang and follow him around while he drives the cadillac, and I fell in love all over again! haha. She was just gorgeous. Eb and flow is how it goes with an old project I guess. :o
I've become attached to most of my cars over they years. Oddly, the one that treated me the best, the '89 Crown Victoria, was always just a comfortable car, with no attachment, while the '83 cougar and '06 Miata treated me poorly, and I was strongly attached . . .
Anyway, everyone is taking the wrong approach to this problem.
Clearly, the answer is to build another garage . . .
Now, as for convertibles . . .
I live in Las Vegas. For nine years, I drove my Miata with the top down about 360 days a year. With 70,000 it probably has 1,00 with the top up.
But I don't think that there's any Cadillac ever made that I could have done that with.
If if the issue is convertible, however, fluid mechanics give the edge to the smaller vehicle, not the Cadillac. Not just smaller, but smaller and shorter.
My '97 Eldorado is noises with the windows open than the Miata with the top down.
The windshield creates a "pocket" in the airflow. Keeping two seats in this pocket is easier than four or six.
So I'll restore my '72 Eldorado convertible, my dream car, but I'll also put an engine into the Miata, as there will be several months a year I can drive it with the top down that the Eldorado will have trouble with . . . (Oh, and it helps that the AC & Heater on the Miata is the same size as a full size car).
Now,, if the Cinnamon hadn't been a disaster, it could have had a roadster variant, but . . .