I bought a used 350(college kid)
Anyway, after getting it rebuild I realized that the rear-passenger side bolt hole was stripped out. I bought a kit to re-thread it and it still leaks oil. It's not a huge problem but I have to check the oil regularly and top it off. Would it be advised to bore and ream a larger hole in the block, or should I just deal with the problem until I have the funds to buy a new engine?

 

A new engine for one bolt?? try some permatex black formagasket. a little around the bolt hole should do it,