Allow me to bring this back to ground for a bit...
You mentioned in you original post, "Bonus points for likely to rise in value." How important is that to you? What is your time horizon for the desired appreciation to happen? In the original post, it sounded like it's not a requirement, more merely a nice-to-have. Of course, I understand the desire to not purchase a depreciating asset, however, significant number of posts seem to have a strong monetary appreciation component to them. If a strong appreciation likelihood really is a requirement within our (in)ability to guess where the future market is going, then I suspect that significantly narrows down the choices, and some of what you are otherwise interested in may not get you there.
As well, you know how it's going. We don't know for sure which direction the macroeconomic situation is going. Perhaps the only thing that trumps greed is fear. The jury is out on if (and when) a US recession is coming soon, and when it does, I suspect luxury assets like entry collector vehicles that you are looking at will drop in value. My personal opinion is that, already we are near or at the peak of an asset bubble; when investment banks are recommending investing in cars as part of a portfolio to their customers, IMO, we've jumped the shark within this economic cycle. How does and how will your timeline jive with the impending recession narrative (if you believe in that at all)? Will things that are out of reach now become within reach then? What if you purchase something within the next year, and a recession hits shortly after, if you care about appreciation?
Now let's actually get to some of the car choices, with my own opinions.
Requirements: Fun, less than 80k miles (this is for judging the price), and not likely to go down in value, will fit in a typical garage. I'm willing to consider 2-seaters, 2+2s, rear wheel drive, front wheel drive, AWD, front/mid/rear engine, trucks, SUVs, etc.
Sounds like you're open. Is one of the primary goals to experience something completely different? Or is something that is very similar to what you already have (say something like a NSX Type R), ok, as long as it meets your other requirements?
Bonus points for low original MSRP (colorado taxes based on that).
How does Colorado treat vehicles that were never sold in the US originally? Would they look up the original MSRP in the home country it was offered in, then convert to USD, or is it based on declared import value, or based on purchase price, or something else?
E30 M3
- This is a great contender. The only issue I have with this is that I personally find it ugly. Otherwise it seems to be something of a sweet spot.
E30 M3 EVO III
- Seems likely to rise in value. Very cool car. Kinda ugly. Too rare and pricey to really enjoy on the road, so how badly do I want a car that I'll be afraid to drive?
Have you driven E30 M3s? I highly recommend driving one before committing to buying one. E30s are supposedly God's chariots, and the M3 is the "best" of them. However, everything I've heard is that they only really come alive and feel significantly more special than a regular E30 when you're wringing them out. So then the question is, how often are you going to wring it out? Are you going to be afraid of driving it hard because of its value, especially the Evo versions?
I would say E30 M3 values have probably plateaued. That skyrocketing in value happened a few years ago, and they are at price ranges where they aren't necessarily bargain values anymore, and for that same price, you can have a lot of different interesting cars. They did a decent amount of these. I only see their values appreciating in the long run, assuming internal combustion engine personal vehicles still have a place in the world at that time.
E36 M3 Sedan
- Great car. They made fewer of these than the coupe, although the coupe seems to be favored by buyers right now.
M3/4/5, especially in good condition, are rare. Eventually there might be a premium of these over the coupe. Not sure we'll ever see much appreciation just because the E36 generation was the middle child between the "legend" (E30) and the "perfect all-rounder" (E46). Also, US models will always be hampered by the "Not true Motorsport engine, wahhh! Europe got a better version, wahhh!" S52 engine. As a positive, S52 aren't that bad to maintain.
E46 M3 Comp.
- Great car. I love the E46. I even own one. The problem with this one is that I'm not just that in love with this M3. Something about the way the shifter feels kinda bugs me.
I think the Competition will command a premium but trend similar to E46 M3. If you really want a special E46 M3, look at Europe only M3 CSL. Not legal to import until late next decade though.
993 911
- Love it. Seems like tons of maintenance.
Ohhhhhhh air cooled Porsches. I'll address the 993 specifically later.
996 911
- Love it less than the 993, tons of maintenance.
Great values if you don't care about the headlights, and are not super worried about appreciation. Regular models have bottomed out, but unlikely to go up significantly just because of how many there are out there. Turbos have been going up in value. GT3 have been pretty flat, but I think they are bargains for what you get, and with limited production numbers, will eventually start appreciating. GT2 are already stupid money. 996s are less of a maintenance nightmare than you think, and are generally pretty reliable.
997 911
- Awesome car, too new.
997.1 are mechanically fairly similar to 996, so your maintenance won't be significantly less. 997.2 might be the most "reliable" Porsches in modern times.
Lotus Elise
- I should probably put some kind of model or year information here. These don't seem to get love in the collectible category. I think this fits my particular driving style, but honestly I've got my driving style covered with my other cars.
Appreciating, because "they just don't make cars like this anymore".
R34 Skyline
- RHD. Beautiful, I'd love it.
Cannot be permanently imported to US for another few years, with the exception of a few existing Motorex cars. Motorex cars are big money because they are Federally legal. Some in the US now are not legal and I would not play that game. Some folks are buying them in Canada/elsewhere and storing them until they become legal to import to US.
R32 Skyline
- RHD. Beautiful (though not as beautiful as the 34). I'd probably love it.
They are fun, especially when boost comes on. Decent selection of them in the US now.
Cayman 987
- Might not be too new (pricewise). I'm not just loving the exterior.
Cayman 981
- Too new.
Cayman 718
- Way too new.
Boxster
- Convertible.
Only ones that I see appreciating over time are Spyders and GT4s. First couple Spyder generations were interesting cars, but weren't really GT cars. GT4s are supposedly great cars, and will at least hold its value. 981 and on only though. GT and GT based cars are going to be where the money's at. If you're not worried about value, then any Boxster/Cayman should be a wonderful drive.
E39 M5
- Great car. Do I want it more than an M3?
Yes. Well, different. M5 is going to be the more luxury GT car feel. They made a lot of these; around 10k were imported to the US. They are at the weird age where you can pick the high mileage, less well maintained examples for dirt cheap, while basically brand new, time capsule examples are going for stupid money. As an all around daily driver, few cars beat this blend. I have no intentions of ever getting rid of mine.
IMO, pricey for clean examples. At a certain price point, you have to think about, what else can I get for the money, and do I really want to spend it on a S2000 or do I want to spend that money on something else?
Ruled out:
Z8
- This doesn't seem like my kind of car. I know that they're loved by the car collection world, but it's not the type that I particularly get. Is it trying to be sporty? Is it trying to be luxury? Is it trying to be showy? It doesn't seem to do any of those badly or particularly well.
It's a retro styled throwback that has decent performance but is really a GT car. Only buy because you like the looks.
The trifecta of "last of the old school" Ferraris:
Ferrari F355
Ferrari 456GT (I've seen these for less than $50k! A V12 Ferrari with a gated shifter!)
Ferrari 550 (These, especially, are going to hit 7 figures in 20-30 years, I'm almost certain. I never understood why people didn't see these as absolutely beautiful when new...as they are starting to now)
This.
F355 will always be hurt by that ridiculous engine out service (mileage AND time based), but has aged amazingly well, and are incredible to look at. 550 is the last all manual V12 front engine grand touring Ferrari built. 575 and 599 can be had with manual, but they are rare, and already command a significant premium. Plus, I think the 550 is the prettiest of the lot. Supposedly maintenance on these are pretty good for a Ferrari. 550 have already been appreciating.
With your budget, look into 360 Challenge Stradale or 430 Scuderia. Very low production numbers and are holding their values really well. More hard edged, racy cars, for the road. Depends on what you want.
I think that the BMW E30 M3 might just be the perfect car except for its looks. It is appreciating steadily, many of them have a ton of miles on them (which means that miles are well tolerated on them from a value perspective). It's very analog and engaged. The 993 hasn't taken off like the M3, and the market for 911s is flooded and continues to get flooded. The 987 Spyder looks like just the sort of car I'd want, except that it's very new, so prices aren't rising. The Spyder is certainly far more attractive to me than the E30 M3.
993 never depreciated to quite the level that the E30 did. The 911 that did exploded in value similar to the E30 was the 964, albeit for different reasons.
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Air cooled 911s will fundamentally be interesting cars that feel significantly different from what you have and own now, from engine location, to feel, to layout, to the view out. People often hold the 993 as the best because it was the last. To that, I don't know if that's true, every generation has their own unique characteristics and charms about them. There's so much hyperbole and expectation and opinions around the 911 generations. Older 911 owners often complain that the 993 is not as engaging of a drive as earlier cars. While 993 owners may scoff at older 911s that don't have head gaskets (and leak oil), or not having the latest and greatest in engine technology.
One thing Porsche had recognize early on is how difficult the 911 could be; by 1969, they extended the wheelbase to help tame the tail. And it continued on, with wider rear tires. The 964 went from a torsion bar and trailing arms to a coil and trailing arms setup in the rear. The 993 took another step forward and went to a coil and multi-link rear setup. The multi-link setup was intended to tame the rear end even further, but some folks will argue that it dilutes the 911 driving experience.
That era of Porsche was interesting because they were running out of money. The 911 had been around forever, albeit with updates through 1989, before the 964 came along for a few years, and then the 993 for a few more years before transitioning to water cooled cars. 964 was a major step forward from the 911, and the 993 was then an evolutionary step.
Porsche buyers can get really picky. Even within the 993 world, prices can vary wildly. Example, early 95 Carrera 4 cabs are worth the least, but something like a later run widebody Carrera S or 4S could be double that value, just for a later model run with a widebody. Add interesting colors and values go up more. Step up to the Turbo and you're suddenly looking at mid-$100k, and so on. Some of the 993 models won't be appreciating for a while, some have already appreciating, and some will continue to appreciate. You would need to figure out what you want and specifically shop for that.
Even though Porsches are well built, and can tolerate high mileage, there are some issues with every generation that you have to be aware of. Parts and labor can get really expensive very quickly. If you need an engine our service, suddenly, cost is significantly higher. There shouldn't be much that requires engine out, but understand what those are and the other common issues to keep in mind.
But that's all the more reason to take the M3 Sport Evolution seriously isn't it?
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