I replace the starter and the battery every twelve months, after living through your scenario the first year. Starter and battery are cheap annual replacements for a classic, and both give you back core dollars. I have headers and have put the heat shield in, I'm certain it prolonges the life of the starter.
But if you are a guy like me that only drives the bird 1-2 times a week, the annual battery/starter replacement is the way to go. Less than 100 bucks due to core return cash.
'68 428 HO M3 Monster, 4-on-the-floor! Need I say more?