To the OP re/ a sleeper suggestion for car #2...an '89-92 Volvo 240. Hear me out.. I know it's not American, but it is...
1. Very dependable with a bulletproof engine. 300k is young.
2. Very simple and easy to wrench.
3. One of the safest cars from that era in terms of crashworthiness.
4. Slow...great for new drivers.
5. Quirky looks that appeal to those who desire a vehicle that doesn't look like every other ToyoSubaNissaForChevKiaHyun compact on the road.
We bought and renovated two 240s for our sons when they needed their first car for college internship programs. They both loved them and kept them for many years, even when they (the sons, not the cars) got to the point they could have easily afforded something "better."
Just an idea. As a previous owner of two early 70s Fiat Spiders, 80s VW Rabbit convertible, current owner of an 80s Benz roadster, and occasional driver of MGs, Triumphs, I heartily endorse the previous recommendations for a Miata unless you really don't mind spending a LOT of dough. Miatas are a blast to drive, ridiculously reliable, and cheap. If you like to drive more than you like to wrench, get a Miata. If you like them both equally, then a lot of the cars you mentioned would be a lot of fun.