Drive Train Upgrade Suggestions

will put an automatic transmission with it so my wife will drive it on long trips.
This will be driven significant distances to events, errands and joy-riding.

There's only three things wrong with a slanty cruiser; cruiser being 2.94/3.23 gears, namely; lack of power, lack of torque, and a really boring, characterless, snoring buzz out the tailpipe(s).
If you get stuck without an overdrive, and cruiser gears, you need a small block, any small-block. No you don't need one like mine, but if yur gonna rebuild whatever you get, it costs nothing more, besides alloy heads. But the very high cylinder pressure will save you money by driving further on every drop of gas. With my daily driver combo, I estimated that the alloy heads paid for themselves several times over in 125,000 miles, just in fuel savings, and in the meantime, 185psi is a real blast to drive.
Before you call me a slant-hater, I have had several, three of the early ones, and a low compression slug later one, that I immediately pumped the pressure up on. I only recently sold this last one, having driven it for most of 25 years.
The fact is; that normally aspirated, you have to really really love them to spend money on them, cuz any V8 similarly saddled with hiway gears will do everything better than the slanty except bore you to sleep.
With your budget, there is no way I would keep that 6-pot........