...By the time I buy all the parts to make this engine original, and get a long block or have this one bored, I can buy a V8 that has newer technology at a comparable price....
I'm not sure I believe that, going back original vs. fabricating and re engineering stuff...
Price
may be similar, but for the amount of work staying reasonably original should be the simpler choice.
You can find all your original parts and perhaps even a good running 235 or 261 from someone who is actually taking the V8 leap, check out the Swap Meet section.
If you go with the V8 when does it stop, will you want faster gears, and OD transmission, power brakes, disc brakes, power steering, fancy wheels??? the list goes on and on.
I've rebuilt one 235 in a reasonably original 52, and am doing the complete new everything on a 48. The 52 was a project in high school, a couple months of work here and there assembling the new engine, and a week downtime switching engines. The 48 is about 5 years and counting..
In the end do what makes you happy, don't worry so much about the cost or work involved so long as you're having fun, will enjoy the truck, and don't second guess your decision.
Grigg