"will the current starter motor"
there is no 'current starter motor'....still to purchase that....probably go with a mini, high torque motor, but shouldn't really be a issue anyway. It would only bring the compression to 9:1 or so, up from 8.5:1. Crate engine 350s run about 9.2:1 or so. The vortec heads are not so much smaller combustion chambers, but rather different shaped (kidney) that produces a faster, quicker, more efficient burn. I think I can see improved mpg...maybe?
"Do you plan on keeping this vehicle - long term? I'd consider this a primary factor in cracking open the wallet. (if you sell, how much of the extra money would you get out of it?)"
This has really been the big question...I am fighting the same question with the steering right now as well...I am trying to hack the old steering shaft back together with the column after having to re-route due to the new motor mount position...It would be way easier to just buy an all new set-up from the column through to the box, but the price is big. It would be way better in terms of both function and form, but what is that worth....if I sell it at some point, I pennies on the dollar back - well maybe dimes if I am lucky.
" It's a 1/2 of the year weekend toy (at most)."
Hopefully as its a hard top with heater etc...it will be a year round weekend toy! Actually, if we like it, the plan is to sell the tacoma and Jen's hatchback, use the willys as my DD, and get another tacoma like truck with auto that Jen would DD....but in reality, guessing the willys will never be a DD...and if it did the next engine (383 stroker) can have roller cam etc...