I use to be a guy that drove my cars into the ground and then purchase a car for cash for whatever I could afford at the time, whether it was $1,000 or $5,000.
One car I own, was in an accident (not my fault) and couldn't open the drivers side door. It wasn't worth the money to fix it. Finally the clutch was going out and couldn't get it out of first. While, at the time, I did almost all of my own car repairs, I didn't do transmissions, so I coaxed it to a junk yard and traded it for a radiator for my other car.
The last car I owned had almost 300K on it before the odometer broke. Both front windows mechanisms broke and would have cost about $300 per window just for the new mechanism, so both were propped up with boards. Up to this point, I really hadn't put much money into the car. Finally the AC went out and it was going to cost $2500 to fix. Couldn't put down the windows and no ac in Phoenix is not a good thing. At this point, I was getting tired of doing my own repairs and tired of nursing cars, so I bit the bullet and purchased a newer "Used" car and had a car payment for the first time.
In the meantime, I met my wife and she convinced me that the thing to do was lease a car and trade it in at the end of the lease for a new lease. always have a car payment, but never have a car get to the point that you have any kind of issues that you have to deal with.
Sold my Newer "used" car to my son and leased a car. Now in my second lease and I am pleased that I no longer have to worry about a vehicle. No longer have to worry about having the right tool to fix things. I have done similar things with home repairs, house cleaning, landscaping, etc. I no longer do any of those things, I pay so I don't have to concern myself with these type of things anymore.