Hey J - I'll try to help here if I can...
1) "Safe" and "worth it" are relative terms. It's hard to know the condition of your engine, so that's impossible to answer. However, your engine is no different than the thousands and thousands of others that need a good cleaning.
2) Here's where you disconnect:
3) 5/16" is the inside diameter of your booster line, but I'm going to suggest you do some measuring on your own for that part.
4) Wouldn't hurt, but I'm not a fan of messing with the plugs over and over - too many chances to cross-thread or damage a plug or the head. It'll be fine with the new plugs.
Good luck and have fun!