my strategy: when you're young and especially if you happen to be buying your first home, buy the cheap version of almost everything as you need it. Minor exceptions for things you KNOW you will use a lot (but they still don't need to be the most expensive). If you like certain jobs, selectively upgrade over the years. If you move a lot or age out of certain things, cull aggressively. Good tools have decent resale value if they're not consumer grade. All consumer grade tools have the same low (but non-zero) resale value IME. YMMV.

P.S. Anyone looking for a quality router with a selection of bits?