Forgive the stupid stroker kit question.

If the cylinder bores are "GOOD" and the block is known good, there is no reason a stroker kit would require any more additional machining than putting a standard stoke crank and pistons/rings in would require. You'd probably want to hone the block at a minimum but as long as you can get your stroker pistons in the diameter your block is at, you are pretty much good to go. Most would probably invest in properly prepping the block to maximize the results. For instance, if you had the block fully prepped and decided to change course and throw in a 4" arm, you shouldn't have to do much of anything.