Isaac. It seems your biggest issue with used cars is uncertainty. I suspect that fear of unexpected repairs stems from not having a repair fund so that unexpected repairs aren't a financial burden.
The advantage of buying used cars is the savings over new. Buying used can save tens of thousands of dollars. The downside of used that are out of warranty is that repairs are paid out of pocket. When I switched from buying new cars to used cars, I continued to pay that used car payment into a repair fund until it hit $5,000. That is enough to cover almost any repair assuming one doesn't go to a shop at tryings to take advantage like the one that charged your friends $9K for a transmission.
Having a repair fund removes the worry from owning used cars.
For example - I recently spend almost $3K on repairs for my 2011 Acura. I paid them out of the repair fund and went on with life. The repair fund will get refilled over time. However, considering I paid $17K for a car that was $50K new, shelling out for a $3,000 repair isn't' too bad in context.
I also spent $5K on repairs for my Duramax Ambulance. That sound bad until you consider a new one is $350,000 and I paid $35,000 for on that was 12 years old with 110K miles.
Part of your problem is likely that you live in the middle of nowhere without many options both to buy cars or to have them repaired. (I'm pretty shocked when you say it is 3 weeks to get a tire repaired and months for a car repair.). I can get a tire fixed in a day and the timing chain on my Acura was 5 days and the owner of the shop apologize for the delay because he had to order in a part that he couldn't find local.
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