Hello Keegstraa. What a delightful and interesting question. The answer could be as simple as purchase the one that catches your eye or as complicated as purchasing a luxury jet liner.
I have been in the automotive field since '72 owning a total of nine cars. The first was purchased for $300 in '72 & was a 1956 Ford Vicky. That & the next four were bought as Hot Rods. Overall the Return on those Investments (ROI) was nil or I broke even, although today they bring a pretty penny.
The next was a practical investment again for $300 only it was '78. My goal was a car requiring minimal maintenance & is very easy to work on for me, a trained professional, or a savy friend. The purpose of the "vehicle" was to go from point A to point B as economically and safely as possible. I bought a 1963 Plymouth Valiant Station Wagon & fixed it up.
Next, it was a new '82 Chev S-10 truck I drove it for 24 years. My goal then was to get the greatest Return on Investment I could get. I had to decide:
What is the purpose of the vehicle
How long was that purpose to be for
When would I be able to purchase another vehicle
What would be the anticipated expenses of repair for that time period, i.e. Brakes, Steering, Cooling System, A/C system, and Fuel/Ignition system
What would be the normal annual maintenance costs, i.e. Oil & Lube services, Tires, Alignment service, fluid replacements, and such like wiper blades. I include tires since there are choices of quality & mileage warranties. Gas would be a living expense and not a cost of transportation.
I would consider those with a new purchase or a used purchase. Ideally my view is you should receive from your investment a return of equal to what public transportation costs are above your investment. In other words if it costs to ride a bus / train "Y" dollars your total annual investment should be 1/2 of that + the "E" Factor. That factor is how much the convenience of a vehicle is "worth to you" in a value, the luxury perspective, independence, and practicality.
Ex: San Diego Regional Adult Pass = $72 ÷ 2 = $36/month x 12 months x 10 years or $4,320. Add an index for price increases to equal say 5% per year. Or, the number is now $5,434.
That is a starting point I would invest in a "around the city/county" vehicle to last 10 years. More repairs means less Return on Investment. Selling the car means an increase in ROI.
Remember, the 2nd greatest investment in the USA a person makes is a car! A house is the greatest.