Opinions please! 1996 Dodge Ram

1997 5.2 5 speed that will turn 200K in the next 2 months.
Most of my wrenching falls under basic maintainence:

I have had some non maintainence stuff
I replaced timing set while replacing the timing cover gasket also.

For me, realistically, anything that has needed work has been AT MOST a Saturday's worth of work (timing chain and gasket day). For me, I would rather wrench on the stuff myself and save the money, then to be in a payment, or drive something that I cannot fix myself and have to pay shop rates, etc.

The architecture is basic small block mopar type stuff. I would not even be afraid to do the intake plenum gasket if it fails, because it is basic wrenching, not rocket science.

I am spooked about the Auto trans, I have heard that they are problematic, but I also know that 95% of the world ignores their vehicles, and the other 5% of us who maintain our rides, might not have killed the trans via abuse, overheat, or lack of maintainence.