We like older cars too but we work on our own vehicles - rest of extended family gets new cars cause they don't like work on theirs.

I think getting the estimates for the repairs you need and see how much it adds up too is a great idea...
plus there is the savings on car ins by only having to carry a minimum policy.

But do the math and take a look at both options.

my car is 84 Volvo nice condition 350,000 miles {we changed the motor at 300,000} but even if we spend 1000 a year on it which we don't LOL it is wayyy cheaper than monthly car payments.
But we do regular maintenance and can tell by look or sound if something is going wrong.

I wish they woulds have classes in high school for all kids to learn the basics of auto maintenance.