I'm a used tool and bargain hunting enthusiast, and when I think about it, I've probably spent less than $1000 on my core woodworking tools.
1. Shopsmith machine with bandsaw, 4" jointer, SS dust collector, biscuit jointer, tenoning jig, 8" stacked dado set, 3 10" blades, and other small accessories - $300. This is probably the best deal I've ever gotten on anything, but it does happen from time to time.
2. Old Delta Rockwell Floor standing drill press - $100
3. Old Dewalt MBF Radial Arm Saw - $85
4. Newer Delta chop saw (36-585) - $60
5. Grizzley Planer - $100. This one leaves a lot to be desired. I wish I'd spent some more money here and gotten one with a locking cutter head.
6. The one place I did splurge was on a brand spankin new (well, OK - factory reconditioned) Porter Cable 7000 series plunge router. I think that was about $200, but the built in height adjustment lets me use it as a router lift when I use it in "makeshift router table" mode.
So that's what, about $850? Leaves $150 for assorted odds and ends.
This answer will probably draw plenty of ridicule, but I say go with a used Shopsmith machine. It's not ideal for every tool, but it is a great way to get started, and you can pick one up for about $500 without having to look for too long. You may eventually upgrade to a cabinet saw, or a standalone drill press, etc., but the Shopsmith is a great backup machine to have in the shop for tools you only use once in a while (the lathe for example, if you only need to turn a table leg on occasion) or to use as a second setup (say dadoing on the cabinet saw and a crosscutting on the Shopsmith). Even if I someday have a shop full of dedicated machines, which is doubtful due to space limitations, I'm keeping the Shopsmith for these reasons.
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