Like you, I too want to get more serious about my woodworking hobby. I have always had enough tools around to do small, simple jobs like a circular saw, miter box, a few clamps and so on. But lately I have wanted to dive in deeper and to some real woodworking projects.
I have watched a ton of video online, trying to learn and get ideas. One thing that has surprised me is tools I have have never owned before, and seemed to get along fine without, are now the tools I seem to use the most. I bought a 10" band saw about a year ago, because I got real good deal at a garage sale. Never owned one before, and I use it almost as much as my table saw. I bought a digital calipers at Harbor Freight because I had a "super " coupon, and have been surprised by how much I use it.
I watch CL closely for good deals, and stop at garage sales, and have saved a lot of my budget that way. I agree with the previous posts, that your tool purchasing should reflect the particular project you need the tools for. But some times after you buy a tool, you wonder how you,ever managed with out it.