Thake an overall view:
Expected depreciation in value + Insurance premium + Expected repair cost + Fuel consumption = Total cost of Ownership
Some of these are a little bit hard to guess, but there are hints.
Depreciation in value: For a normal everyday vehicle, this is quite easy - the less it costs, the less it will lose. Beware of vehicle going against a trend (like diesel in Germany nowadays). This may not be true for older sport scars and specialty vehicles, but those mostly dont perform well in the running costs or just aren´t practical. Here you have to weigh the added comfort of a newer/higher class of vehicle vs. your willingness to pay for its value depreciation. Resale value in general does not matter so much, because it´s buy high & sell high vs. buy low & sell low.
Insurance premium: Just get a quote, and you´ll know exactly.
Expected repair cost: There are three thing to this. First, you have to have a good repair shop available, which is proficient with this brand/model - else you pay extra on work. Second, volume models and domestic manufacturers tend to have cheaper parts-prices, but that may also vary. Generally bigger and more expensive (new) a vehicle is, the more expensive the parts are. Third: There are often know weaknesses or expensive services due. Look what applies to your candidate. A good source of information for all that is usually the mechanic who will be making the repairs, but also googling for common problems with a specific car tells you what to look for.
Fuel consumption: You know how to calculate this. Depending on how much you drive, this factor matters a lot or almost not at all. Don´t trust the manufacturer, get real-world numbers to calculate your fuel consumption. We have a site in Germany which gives you user-generated statistics on this: spritmonitor.de/ - I don´t know if you have something similar in the US, but google should know.
Bonus Things like cosmetical damages may give you a better deal when you buy the car, but won´t hurt as much when you sell it, as the older a car gets, the less those matter over the pure transportation value.
And last: congratulations it is almost always wise to buy used and cash over new and financed, money wise. some of us take years and 1,000s down the drain to get that.