I acquired my tools one-by-one, as needed for the project. When I got married, I received a hand saw as a gift. I then went back to college. During my college years, I added a hand drill and a skillsaw, total cost: $50. Using these two power tools I made a picnic table with 4 benches, a doghouse, some bookshelves, a waterbed frame and headboard, a computer workstation, etc.
Years later we bought our house and wanted to make a deck: I picked up a Ryobi sliding compound mitre saw. The skillsaw "could" have worked, and WAS working initially, but the "chop" feature, and mitre capability of the Ryobi were huge time savers.
Then I tried my hand at making a classical guitar, and thought a bandsaw would be handy. I traded the mitre saw to a friend who had a small 14" bandsaw. Somewhere in between there I got a router for Christmas. I also bought a small (14") Delta benchtop drill press ($79). That bandsaw and drill press (with sanding and planer attachments added later) were huge time savers, and to this day are often used. Oh yeah, a small Delta benchtop belt/disc sander too.
During guitar #2 I bought a used Crafstman TS for about $150. It was a direct drive with bad bearings, so I ended up selling it to someone who merely wanted to chop 2x4's (I needed to make exact cuts to the nearest 0.001" in Rosewood). Still don't own a TS, but have been borrowing a friend's, same guy who has my Ryobi mitre which is really miss; will probably buy it back! (indeed, we recently added a second deck and I had to borrow it back from him!)
While making my guitars, it became apparent that a thickness/drum sander would be SO useful, but alas, too expensive to justify, so I continued doing things by hand. More recently I began a project of making a full set of "mission style" furniture, so I finally picked up that drum sander, plus a Dewalt planer. These two additions have become real favorites; I can't imagine the time it would take without these tools. But they make a mess, and the 'ol shop vac just wasn't able to handle the amount of dust generated by the drum sander. So I had to buy a good dust-collector (Jet 650CK with 2 micron filter). I also "needed" a 6" jointer for my furniture project, so I bought that too (used for $175). At this point I should mention my 2003 tax return has been spent in advance!
Well, that's my long-winded way of saying, "pick a project and THEN decide what to to buy." I once read that famed luthier Jose Romanillos built his first classical guitar on his kitchen table using a few chisels and a knife. Today he receives something like $20,000 per guitar, and has a waiting list. Point: you don't NEED every tool stocked at Woodcraft to make something nice, though having them WOULD save time. I still don't own a TS, having loan of my friend's saw. For what I'm doing, if I had to choose between a bandsaw or a TS, I'd pick the bandsaw as it will make the same cuts I'm making with the TS. However, I DO plan to get a TS within the year, but note that it wasn't the first thing purchased!
Cheers,
Scott