1 - It can be. Technically any adjustment or maintenence at all it should be reset.
2 - Technically yes, realistically, no. Just use your best judgement. If it starts acting funny after a mod or change, reset it.
3 - Oh yeah, it needs a re-flash and a reset. Re-flash programs the new ecm to the bike.
4 - The real deal Buell stuff is near impossible to get unless you are a dealer or big independant shop. I havent played around with TFI boxes enough yet to know, but I have heard you can do quite a bit with those yourself without having to take it in.
4