HMMMMM -- good question.
1) books on the tools/equipment you would like to purchase.
2) Shop Vac, 3) Clamps, 4) Handtools - saw, chisels, planes, tape measure, straightedge, etc.
5) circular saw, jig saw, router - combo kit (either Bosch or Porter-Cable) do not cheap out on the router. You can purchase a fixed base Ryobi and learn with, but plan on the other within the year.
6) Drill press, orbital sander, 8" grinder, belt sander.
7) now is the time to look into a Table Saw -- multiple choices.
A used Delta or Jet contractor saw would be a good start.
8) Planer, Bandsaw, Jointer ?????
Everyone will have different opinions on this.
Good luck and be safe, Randy from Oceanside, CA near the Firestorm
Frankly, looking back, I think the FIRST thing to do is to join a local user group. Get with folks who have tools and do woodworking. That's the best $20-30 you will ever spend, finding other woodworkers.
After that, find a project. Buy the BAREST minimal set of hand tools needed to do that job. You do not have to use power tools all the time. Many woodworking groups have swap meets, go to them, save oodles and get help from new friends.
The real regret I have is the years I spent with the usual setup. Most of it was unsafe and wasteful, especially long term. Safety is NOT trivial when you have 20, 30, 50 years of tool use ahead of you. I sure hear a lot of coughing in my local woodworking group from guys who saved money not buying air masks. And a lot of guys who didn't bother with hearing protectors are wearing hearing aids now. Buying cheap tools was a bad idea totally. Don't "work your way up," that doesn't pay.
If you are not all tooled up and can take the hit, I say forget the old fashioned advice about spending all your money on the biggest, baddest table saws and blahblah. If you can swing $2,000 or so, buy a Festool "everything" kit, with saw, router, sander and their special work table setup and a big dust vacuum that really works. Right from the beginning, avoid toxic dust and do PRECISE work. Long run, I think the Festool kits are the biggest bargains. If you find out in a year you don't like woodworking, you can sell it for nearly as much as it cost. Compared to that, you could spend hundreds on cheapo tools, find out you don't like the hobby and get ten cents on the dollar for used junk.
If you absolutely can't afford a Festool kit now, buy a SMALL Skil circular saw and build a small work table to cut sheet goods. Also decide that you can use pocket hole joinery until you have a hundred bucks or more to put into clamps. The nicest addition to my saw collection ever was that tiny Skil 5.5" circular saw.
I have many ideas on low-budget tools and workshops, actually. It's a fascinating topic for me. I've made a specialty of finding extra-value tools.
Here are the best tool investments that I have made in my experience (note: I have done dining and living room furniture, house trim and floors, sundry outdoor projects, and a lot of hand tooled/carved gifts):
Best Value in my woodworking quest: Danford Jennings' "Shop Notes" series that are available through the archives of this forum for free.
Wet dry sand paper in grits between 320 and 1200. 3 in 1 oil. A sheet of glass. This sharpening system is my single best investment. Because of it I have been able to finally effectively use chisels and planes.
The Shark saw. A $15 disposable blade "japanese style" saw that I bought at the Depot has been fantastic for my hand dovetail work.
The book "Table Saw Basics" from the Taunton store...which is a compendium of table saw jigs, tips, and techniques from Fine Woodworking Mag.
The book "The Encyclopedia of Furniture Making." Best Book Ever for furniture making, joinery, and woodworking in general, in my opinion.
Nearly every issue of Fine Woodworking...it keeps me excited, motivated, challenged, and intrigued.
Rip blade for my table saw. Sounds odd, but I feel a hell of a lot more safe now using this tool.
Bosch 1617EVS router dual base kit. Though I use the router less than some, this is a fantastic tool. My woodworking changed completely when I got this tool.
Planer and Jointer. I save a lot of money by having both of these, and combined with my table saw I can do whatever I want to rough lumber short of resawing wide planks.
Makita Random Orbital Sander. Still running great two years after spending $60. When hooked up to my 2.5" hose shop vac, this thing is operates with very low dust.
Stanley combination square. I searched around on this one, and to me the $13 I spent there has paid me back in spades.
Shop Vac. I know most people say the DC is critical. I totally agree. But for sheer value, the shop vac is unmatched for me. I have a very small shop and had to make a hard choice about dust collection. I cannot spare shop space for dedicated DC lines, hence, I only use the big DC on three tools. All the rest of my work (and especially my house work) is shop vac assisted and it is a great tool. Plus it saved me around $5000 last year during our 50 year flood. In addition, I clean my gutters with it without using a ladder or going on the roof.
Finally, you've found this forum, so hapiness with wood is not far off.
Regarding the local wood club. I joined one in my area a few years ago and decided not to rejoin. Sadly, it was a very judgmental, hypercritical, beaurocratic, and macho tool fest that I was glad to be free of. I'm sure others are better, but the time I spent not driving an hour in traffic was more time in the shop.