Currently looking to buy a new car, here are a bunch of cars in my local are that I'm considering buying. I'm willing to spend a bit on upfront repairs so age doesn't matter a whole lot, And I only commute about 5 miles round trip for work.
1989 Honda Accord w/ 181,000 Miles - $1,500 (Cool little commuter, love the Hidden Headlamps and style, I live far north so would the Carburetor give me trouble?)

1995 Toyota Celica w/ 121,000 Miles - $3,500

1996 Honda Civic Del Sol w/ 171,000 Miles - 3,700

1992 Mazda Miata MX-5 w/ 208,000 Miles - $3,500 (Engine Swapped at 150k miles)

1998 Honda Prelude w/ 200,000 Miles - 2,500 (Owner says damage is purely cosmetic, car is mechanically sound hence the small price.)

2001 Pontiac Firebird w/ 192,000 Miles - $3500 (Owner has two Firebirds, hence the slightly lower sale price.)

1985 Nissan 300ZX w/ 178,000 Miles - $3,500 (This is the wildcard, popped up yesterday, and this car looks fucking insane. Owner says he's daily driven it for the last year so would this be decently reliable? I'd especially like details and ownership experience/information about this car)

Amongst these cars which would be the most reliable over time, cheapest to maintain, and can anyone shed details on the individual cars? Problems with models maybe that would make them subpar choices? Or some to just avoid altogether?
Man those are all pretty old. Hard to say what the reliability is nowadays. I would avoid the Nissan, the Firebird, Celica, Prelude, and Accord. Jeez. I'd honestly avoid them all and get something newer with lower mileage.
Normally a Miata is a good bet but that one sounds like it has had a hard life. I can't really recommend one off that list.
The Del Sol looks to be in really good condition. Keep in mind any car that is 20+ years old won't be completely reliable.
Get whatever you want inspected by a mechanic before you buy it.
Without a doubt, Scotty would tell you a Celica. He's fond (perhaps overly fond) of pointing to his Celica with 240K, as a pinnacle of reliability. And you could always ask him directly for advice about this model, since he has a long history with a mid-90s Celica. Then, perhaps the Civic, Prelude and Mazda Miata.
Personally (and this is just me), the Miata's too small and vulnerable a vehicle.
As for Pontiac, they are long since gone, and for good reasons.
A 300ZX, even a 1985 model, is overkill for five mile trips. That's not how they're meant to be driven.
But don't believe a word about damages or repairs (or even engines) that a seller might make. It's all a bunch of claims, not fact. Whatever you decide, get a pre-purchase inspection. And if it's one of these older cars, make sure your inspector is old and experienced enough to assess cars that may be as old, if not older, than the potential inspector.
Good hunting.
I find it's really hard to find cars I like beyond the mid/late 2000s
Considering the age, and obvious repair payments that would follow any of the cars, which would be the most reliable for it's time? I'd imagine the Celica or Miata. But I'd honestly be willing to deal with some extra expenses instead of a 2010+ car. What kind of headache should I expect? I currently daily drive a car that's 19 years old and it's never failed me, or needed serious repairs in years.