Daniel,
I bought a Stanley #4 and #5 for about $20 each from eBay for my first tools. They I got a set of 750 Chisels on eBay though I was only looking for two or three that I really needed. Eventually I looked around for old rip saws (since rip saws will do fair at crosscuts but not vice versa) and bought a D23 for about $6. I bought a Sterrett square which I knew I would have to have. I also bought some F-style clamps of various lengths but only what I knew I would need for this project.
I was very blessed by kind family members who bought me Norton water stones (with a honing guide to go with it), a chisel wrap, and a Lie Nelson tenon saw for Christmas. I also bought the Veritas dual marking gauge, a Stanley 62 folding rule, and a couple other small items that were helpful but I know if needed I could do without. For my birthday I got a Lie Nelson No.60-1/2R rabbet block plane. I would have made due without the tenon saw or rabbet plane but they have been very helpful.
In the last couples weeks, after 9 and a half months just working with only those tools, I have bought files and saw set to tune old saws, I bought bow saw pins and blades (which I will also use as a coping saw), I bought a lot of 10 saws on eBay for about $70 but all are old Disstons, I bought a bevel square on eBay for $9, and I bought 4 keyhole saws on eBay for $10. I have not received all these in the mail yet and have not had opportunity to use any of them. Though all these items are ones I could really use on upcoming projects with the exception of the 10 saws (that’s a lot of saws). All the prices I gave were including shipping. Right now I feel that I am at about the point where I feel I could tackle whatever project I wanted without much difficulty.
I would like to only buy enough tools to fit into a traditional tool chest and a saw till. I believe my next big purchases will be for bench vices as currently I have just been using my F-clamps or plane stops to clamp wood to whatever surface has been available for working on.
There are a couple of other items, like a mallet (at the moment I use a rubber mallet that I already had), auger bits, or holdfasts but I’m unlikely to really work towards trying to buy bigger ticket items like carcass saws, dovetail saws, fore or jointer planes, or routers until much later. I am crossing my fingers that my family may be generous this Christmas again and get me a Veritas plough plane.
I’ve been lucky to find some deals around but overall I’ve not spent that much each month (though almost all my spare money has gone to tools). I think that has been my overall journey and plans so far in getting tools for traditional woodworking. If you have any questions or want pictures of anything just let me know.