Venting some fusterations and possible ideas/solutions

Don't bet on it. Overhaul an engine, and you've just eliminated any profit when selling the airplane.

You can certainly buy an airplane and finish primary training and sell it without having to overhaul an engine.
 
I have seen students buy an airplane to save money. The airplanes they could afford turned out to need so much expensive work that they saved nothing, and recouping all the costs was pretty much impossible.

Many buyers find that their first annual turns into an expensive headache. Never forget that you're buying something that someone doesn't want anymore, or couldn't afford to maintain it properly. In either case, money that should have been spent on it over the years was not spent, and you might have to spend it instead.

That’s if you buy anything wrong.

A proper prebuy eliminates most of that.

I bought my first plane to build hours for my CPL, it was a great plane that I kept for quite some time, took a upgrade to a much more expensive plane to get me out of it.
 
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