There are some great suggestions here. Thanks, everyone. And thanks for the advice, too. I figure I'll start with a few $5-10k examples, sell those occasionally to move up in price range. I'll have space for five I think, but there are easily 30-40 I'd like to have, so I'll probably rotate cars in and out every so often. And they'll definitely be stored in a proper garage with temperature and humidity control. This won't be Roadkill Garage.
You only make money when you sell.
If you must own a collection, and you do not want to lose money, I would suggest that you buy the best example of any car that gives you a thrill, and immediately and constantly be on the look-out for a buyer who will take it off your hands for a set profit.
The "profit" can be either a set monetary gain or even just the thrill of having owned/driven a certain vehicle; if i could own, drive and recover my money after driving a Ferrari for a year, I would be thrilled; beats the hell out of buying a new Honda, eating 25% depreciation and only having the experience of driving an appliance to bask in.
I also think that a very good condition 95 Range Rover classic is going to skyrocket in the next 10 years. I'd suggest a green or black one.
John Welsh, amen on the 'V' and 'SS'
Integra Type-R (or a nice GS-R), LS1 Camaro/Trans Am (bonus for SS/Firehawk/Anniversary), Ford Lightning (either one), Syclone/Typhoon (really any of the turbo-6's), clean 240SX? , clean MR2, earlier gen Supra/RX-7.
I would imagine quite a few of these would be pretty close to the upper threshold of your budget (some obviously a bit above if in great shape with documents). Obviously my list is biased more towards the 90's-2000's, as others have said I'm not sure how much longer the 60's will continue to appreciate as they have been (and a lot are out of the $5-10k range already).
NOHOME wrote: You only make money when you sell. If you must own a collection, and you do not want to lose money, I would suggest that you buy the best example of any car that gives you a thrill, and immediately and constantly be on the look-out for a buyer who will take it off your hands for a set profit. The "profit" can be either a set monetary gain or even just the thrill of having owned/driven a certain vehicle; if i could own, drive and recover my money after driving a Ferrari for a year, I would be thrilled; beats the hell out of buying a new Honda, eating 25% depreciation and only having the experience of driving an appliance to bask in.
If you're thinking about owning a Ferrari for a year, this is a good read.
My question would be when do you plan to sell these cars? For example if you plan to hold them until say 2030 and then start selling them you need to look at cars that were popular around the year 2000. Why? Because people buying older cars are trying to relive their youth. And the guy who lusted after a car when he was in his teens or early twenties will finally be able to afford a nice one when he's about 50. This is why muscle cars of the late sixties and early seventies Skyrocket in value once they were about 30 years old. Guys who couldn't afford one when they were new are now at an age and earning capacity where they can indulge themselves.
Think this is poppy cock? I must admit I looked at your profile and see that you are 48 years old. Look at the list of your potential candidates in your original post. With the exception of the C10 pickup all the cars you list were desirable to you and new when you were in your mid teens to early twenties. Am I wrong? LOL
My hypothesis is made if you want to buy something that appreciates somewhat and is not exotic.
And I disagree with no home. You make your money on a classic car when you buy it not when you sell it
On thing to consider - you have to park them somewhere. Unless you have a free barn on your property, you'll need to factor in storage cost. And you'll have to pay for maintenance, even if you do it yourself.
Personally, I don't see the Porker market go anywhere right now other than very special examples, and those aren't $50k cars, let alone $5k cars. The trick is to find out what's going to go up in a few years, not buy after the prices have already been going up for five-ish years.
What car do you like, and can picture youself working on- spending hours to make it perfect?
That's the car you should get.
Plan that a retirement car will never be sold. The odds are higher that you will die before you sell it, so it should be about your enjoyment and NOT investment.
I retired last monday, on Tuesday I registered a 2002 Mercedes SLK that I bought over the winter as a reliable retirement fun car. I've spent most of the last week completing a restoration project Spitfire for my oldest son. Next week the 63 Spitfire race car gets woken up for the start of the season (Limerock June 1st). I drove the 70 GT6 to my last week of work, too cold for the 80 Spitfire convertable. I think a small car collection, balanced by actually driving the things, is going to be a good way to spend the next phase of my life. Haggerty classic car insurance for the 4 cars is under $500 a year (including the race car trailer). I'm sure I have under $40K in all the sports cars (= one used Lexus)but much more fun.
mike h
BoxheadTim wrote: On thing to consider - you have to park them somewhere. Unless you have a free barn on your property, you'll need to factor in storage cost. And you'll have to pay for maintenance, even if you do it yourself. Personally, I don't see the Porker market go anywhere right now other than very special examples, and those aren't $50k cars, let alone $5k cars. The trick is to find out what's going to go up in a few years, not buy after the prices have already been going up for five-ish years.
I made my four best deals on air cooled Porsches in a hot market. You can still make good deals in a hot market, it's just harder, but the upside to that is you don't have to have a crystal ball because they're already hot. Sure, most of them the buy in was high too, but one was a super clean, non running (now running) 914 that was definitely in the listed price range.
In reply to Ovid_and_Flem:
This is good advice - the Model T crowd is long gone and at one point it was thriving. I don't want a Model T or A but a Datsun 510 or 240Z? That was hot when I graduated high school in 1980 and now that I have a little money saved? The wife wants to redo the kitchen.
In reply to Cotton:
I think it depends on how long you want to keep the cars. When I hear "retirement collection", I automatically assume "long term". For that, Porsche might not be the best choice right now.
For shorter term collecting, I'm with you.
In reply to BoxheadTim:
Good point. I plan on keeping a few, because I just love the cars and the era, but really hard to say what they'll continue to do. I kind of think they'll continue to creep up, but I'll be surprised if we see another sharp rise like we saw over the last several years.
You know what has recently shot up in value that you never hear about? mid to late 60's Mercedes. What you could buy all day long 7 years ago for 10 to 15 grand is now 80 to 90 grand. Why? they are cool and stout. built to last and be repaired and run. If you pay attention, you can capture the right cars at the right time. I bought my e28 M5 for barely over 4 figures in 2010. At the time I knew I paid just a bit much but I knew it was in good shape and well built and I thought it was cool as hell. If I never sell it I'm happy. You know what I'm looking at now? A local Jaguar xj-s for under 4k with 130k miles on it. I've always wanted a v-12. The only reason I don't already own it is it's an automatic. So it goes. If there's a car you thought was cool, that's what you should buy. You aren't the only one that thought that.
In reply to gunner:
You're right about the 60s Mercedes. Those snuck up on me and I was like 'what the hell just happened'. However, I did just buy a 59 190 4 door, which is still basically worthless and will probably stay that way. 
Did anyone catch the early 80s 300td wagon that went for 32k on bring a trailer? I thought it must have been a zero mile time capsule, but no it had over 100k miles and was nothing special. What the berkeley? That was an odd one.
Yeah, that 300td was definitely oddly priced. I thought it might make something like $15k, but over $30k?
I think the reason was that while you can find grotty ones all day long, a really nice one is becoming almost impossible to find. And that's the sort of car you'd want - used to be plentiful with a good reputation and all of a sudden they all disappeared.
For something that old, the extra 2 cylinders add a ton of value. Back in the day, every unit of power came from added cubic inches. turbos superchargers and carburetors were not a fun mix. Today's 70-year-olds typically don't want to deal with that combo.
I think the Nissan/Datsun Z cars work well for this purpose. There were enough made that it's easy to find neglected examples, but they're desirable enough that collectors are willing to pay top dollar for a good example. Parts are not outrageous, and they're easy enough to work on. I've owned a few and on each one I've sold it at a profit after driving/maintaining them for a couple years. Anything Z32 and older will only be appreciating at this point, and you can certainly find ones in the low end of your range in running condition.
In reply to Ovid_and_Flem: You make a great point about wanting cars from our youth. I'll definitely keep that in mind. As to when I'm going to sell them, I'll have space for five but want 30-40. They'll be rotated out from time to time as deals come along.
In reply to BoxheadTim: No worries, they'll be kept in a climate controlled garage. As I said before, this won't be Roadkill Garage.
In reply to alfadriver: I'm keeping projects and the collection separate. The list of vehicles I want as projects is even longer than the list of those I want in the collection. If it's in the collection, it's already been sorted. Not to say that a project won't end up in the collection though.
In reply to OFracing: That's fantastic, Mike. Way to go.
In reply to Ovid_and_Flem:
Are you wrong? Maybe, maybe not... 48 years old is squarely in the Gen-X age range. Our interests tend to be all over the map. I'd argue most of us lean more towards 60's & 70's muscle cars more than the "malaise era" cars of our youth.
Either way, I still have a fear that within 10 years or so there will be more collectible cars for sale than the market (younger buyers with the means to purchase and keep them) will be able to bear. Especially in multiple quantities.
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