New challenge: 10k USD for last-half 20th century cars Vehicles at 10k or cheaper from 1950-1999. I'd personally pick this $7,995 stock Porsche Boxster convertible.
1997 MB E50 AMG for $7500 New challenge: 300 or more hp for 3000 or less dollars My pick: Cadillac Seville STS 4.6
Answer to the old ones if you want to, and here is another: $150 cars. Have to be working and roadworthy. As usual, we have discounted JDM stuff (namely, a $116 V8 Jaguar S-Type - https://www.beforward.jp/jaguar/s-type/bf929225/id/1018297/), but as I feel it is a bit game-breaking by now, I'll go for what you can buy for that kind of money - a 90s economy car. And I'll go for the fanciest one in the economy price segment, a Daewoo Espero:
I found another vehicle with a even cheaper price: a good condition 2005 Volvo V70 for $30. https://www.beforward.jp/volvo/v70/bf881267/id/1010653/
I pick this Ford F-150 Lariat. https://www.truecar.com/used-cars-for-sale/listing/1FTRX18L4YKA57244/2000-ford-f-150/
US$1000 3-row family cars: After considering some 90s minivans (most notably Toyota Previa), Volvo 940, Toyota Mark II and old GM wagons, I choose a 90s Chevy/GMC Suburban. Nothing more spacious and capable at the price.
$2k USD performance cars: An automatic JDM 2003 Nissan Fairlady Z - https://www.beforward.jp/nissan/fairlady-z/bg039365/id/1088017/.