On the money issue one`thing I did is find something that is fairly easy to make and easy to sell. I made kaleidoscopes to begin with and still whip up a batch if I need to buy wood or a new tool. A neighbor WW makes wooden condiment holders for restaurants. A good friends son worked his way thru college by making a certain bearing that they needed on his tiny lathe. Spend a month or so on $$$ stuff before doing the better stuff.
If you choose paint for your finish, you won't want to waste your money on woods known for their color and beauty when stained, so avoid richly-colored species such as oak, maple, walnut or mahogany. For painted projects, poplar is a very good choice because it is relatively stable and takes paint quite well (not to mention that it doesn't look all that good stained).
Every woodworker needs a couple of levels. You probably won’t need one of the 6-foot levels used in construction, but 48” is a good length for many of the woodworking projects you’ll do. Usually, you’ll also need an 8” level too, usually known as a torpedo level. You’ll check the level and plum of your construction. Level means horizontal, and plumb is vertical.
Just how small?  Will you have an extra bedroom for your shop or will you be doing woodworking in your living room?  Do you have to put the projects and tools away every time you want to entertain or will you leave everything set up all the time?  A while back FWW had a video tour of a shop in Japan that was smaller than small.  I'll try to find it and get back.  Found it...  shows what can be done in a small space but this shop was not on a small budget so no help there.

Flea markets and swap meets are great sources of old tools, but unless you are able to rehab and sharpen them, they aren't going to do you much good. You can always find lots of chisels and planes at these places, and they can be brought back to life. I wouldn't waste my time on any saws though, unless they are relatively rust-free. If a saw is rusty, you will have to re-file and re-set the teeth, which requires a good deal of expertise and some specialized tools.
Steve Ramsey.  He's an energetic, fast-talking eccentric whose built his channel based on projects that can be done without investing in fancy tools.  He trudges out a banged-up table saw from his garage, chops stuff up on the bed of his truck, and generally produces well-structured projects - even if I can't agree with his design aesthetic and color choices.  Lots of good stuff to learn and a great channel for someone starting out.  

"Woodworker's Supply, Inc. failed to properly investigate these complaints and failed to protect Ms. [Teresa] Logsdon from illegal sexual harassment, and gender discrimination in the workplace," according to the complaint filed by her attorney Wendy Owens of Casper in July. "Ultimately, Ms. Logsdon had no choice but to give notice of resignation to protect herself." 
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