Which Classic Sports Car?

At 47, after a lifetime of dreaming, planning and more dreaming, you would have thought I'd have figured out what car was for me. Somehow, now that I finally feel comfortable pulling the trigger on something I seem to be suffering from decision paralysis. It would be great to get the input of others to help with this decision.

I'm comfortable spending up to $20k, but could be convinced to spend more if I can feel confident I could get the money back out of it if needed. I've always assumed my first classic would be an early 70's British/Italian/German but again, could be convinced to look outside of this. Here's my shortlist...

Fiat Spider - possibly the current list leader, seems more usable than some others on the list, good looks, decent aftermarket

Triumph Spitfire - good looks, I love the flip front end, simple, maybe more of a "toy" than the spider

Triumph GT6 - been on my list since I watched one rust away at a local gas station as a kid, love the looks!

MGB - my limited experience driving one surprised me with how nicely it drove, does seem a little "vanilla" as there are lots around

Porsche 924/944 - most "driveable" on my list, possibly more complicated & $ to maintain, later cars seem to "new"

The list probably reveals I have a "type", but please don't hold me to it. I'd love to hear what you think i'm missing...or what you think about anything on my list.

Thanks! 

I'd include the 1960s or even earlier on your list. The 70s were a bad time for cars in general - snogged and down on power.

Fiats - the reputation of the old ones for rotting is absolutely correct, but if you ever found a restored (and rustproofed) example, worth considering.  Ditto for Alfas.

Spitfire - small, cute and early ones had interesting handling quirks.  If you want cute, small and reliable look at a Bugeye Sprite.

GT6 - nice sounding and nice cars but similar suspensions issues as the Spits plus occasional gearbox issues.

MGB - understand the vanilla comment. The  MGB GT is an under appreciated car for long trips, and the six cylinder MGC is excellent for that.  The earlier MGA is a prettier car but the compromise is that it uses side curtains instead of roll up windows. That ay not matter to you if it is a sunny day car. The MGA coupes are great for civilized touring if you are OK with not having a drop top (which I assume as you mention the GT6). Rarer but also very good tourers - pic of mine below.

Porkers are OK, more expensive to own and maintain, though.

The easy answer is a Triumph TR8.  No better bang for your buck.  Prices are really starting to climb, and I suspect they will soon go thru the roof.  Many of them are being sent back to Europe and Australia where they are being sold for two to three times their purchase price here in the states.  A lightly modified one will run with just about anything out there and absolutely pants anything else on your list.  For the last 30 years I have been finding and restoring abandoned, forgotten, barn find TR8s.  Its almost impossible to find them now.  So many of them have seen very high dollar restorations.  If you want to go cheaper, TR7s will still out perform everything on your list and you could get 3 or 4 really nice ones for your $20K budget.  Here is the latest one I finished.  Was thinking $12,00 for it while I was restoring it, but now thinking somewhere in the 16 to 18 range since the prices keep going up.

I would vote for the MG. Out of the ones you listed. Out here in the area of the "four corners" you can get a decent rust free one for a decent price. How about this one?? I know it's not a MGB but....

https://denver.craigslist.org/cto/d/denver-mg-midget-race-car/7475825082.html

Thanks for the input!

Not sure why but TR 7's & 8's don't seem to do it for me.  There's certainly more performance there than in some of the options on my list, but this is more just about fun than actual performance numbers.

I went to see a '75 Fiat Spider today and went away a little disappointed.  It was surprisingly rust free, as I live in Southern Ontario and nothing is rust free here!  The engine started up nicely and ran well too but the driving experience wasn't what I expected. It was the first Spider I've driven so perhaps it wasn't a great example.  I'll definitely try to line up a drive in another one.

I also contacted a the owner of a '72 Spitfire for sale. He's away for a few days but hopefully I can have a look at it when he gets back.

In the meantime the search will continue. Any other suggestions or thoughts on cars already mentioned are welcome.

Thanks!

Alfa spyder

914 Porsche

65-69 Corvair

is a 65 Mustang a Sports Car ?

What about Morgan or Lotus Seven/Caterham/whoever else licensed the chassis? Neither changed much through the decades, so at least you shouldn't be locked into a particular era. I think. I honestly don't know much about either, but that's the impression I've gotten. 

Is a Datsun 240Z possible?

I had a '71 MGB GT I loved, but the dealer turned the shop over to his kid (who was an asshat) and suddenly the parts I ordered and waited months for went to his friends.  Sent the car down the road, but I still miss it sometimes.

Dealership was gone 18 months later.  Karma is a bitch and all of that...

It's tough to make a recommendation without knowing you and understanding what you really want as a result. 
I have owned MGB GT, 944, Healey 100-6, Triumph TR4, MG TD, 280z which fall into your bucket more or less. 

If you want nostalgia but some semblance of comfort, I would do the TR4. I loved mine. 
If you want a truly incredibly handling car, get the 944...hands down. 
The one I kept is the 100-6. 

914's are pretty scarce around here, I think most have become one with the ground once again.

MGB GT's & pre-80's Alfa's are definitely of interest. If one came along I would definitely have a look at it. An MGB GT with a Sebring kit is on my bucket list.

240's have always been a favorite but prices are ludicrous now...like multiple exmaples around for $75k+.  Not convinced that's a solid investment and at that price it would have to be.

TR4's are also appealing but nothing available within a days drive at this point. Wouldn't be surprised if prices have climbed higher than i'm comfortable with on these.

Nostalgia has been a priority. If that changes I think a 944 would be the car to with.

Any thoughts on the cost of living with a 944? A Spitfire for example is obviously not as useful, but is still fun and is very simple. Parts are cheap too. 944 parts I suspect are not quite so cheap. Are there specific 944 mechanical issues to be watching out for?

Thanks

I see you are in Canada, so I have no idea how prices might compare to my neck of the woods.

Near me (mid-Atlantic Washington DC-Ish area, there is an excellent used 944 source, "Just Joshin'". It's a 944-only graveyard and almost anything can be had reasonably including entire engines. I just bought an engine for a friend building his first race car...$500. 
Cheap parts cars can still be easily found which is a good idea. 
AFM, ECU, normal wear items...I kept spares of these. The engine is notorious for blowing timing belts and wrecking top ends, so that's a good first thing to do. It is essentially half of a v8, so it has a balance shaft to reduce vibration...that trips folks up but is no big deal. All aluminum requires a little special treatment, but it's not bad...just different. Fuel rails are getting old so I like swapping those out. Again, my experience was racing them, but a few have been in the family as daily drivers. 
What you get is a beautifully handling, handsome car that I believe is aging very well. 
If you go that route, let me know. There is a solid group of knowledgeable members here...and my son owns a 944 restoration shop. 
 

If you do your own work and find a good source for quality used parts, it is reasonable to run and own. If you're paying a shop, be prepared to plan a budget.