Ok, the leap from $1,000 to $2,500 is a big one.  I certainly didn't make it at one time.  It took me years.  But I know folks that decided they wanted to get into woodworking and dropped at least $2,500 getting themselves outfitted.  When you do make the jump, the thought process becomes much less about making sure you can get the job done and becomes more about having quality tools to get the job done.
Just like a hammer and tape measure, a drill is something a lot of people already keep on hand for small household projects. Danny and I started out on a SUPER cheap drill when we first got married and quickly learned that this was not something to cheap out on.  If you plan to do much woodworking, invest in a quality drill.  It doesn’t have to be the best of the best, but do at least get a mid-grade drill.
Just a little nitpick on the tape measure blurb. The hook should not be completely tight. It should move in and out about a 1/16th or the thickness of the hook. This way you get an accurate measurement whether you hook a part to measure or bump up to it. If you want more accurate measurements with a tape measure, “burn” an inch instead of hooking or bumping the part. Just line up what you want to measure with the 1″ mark and subtract that inch from the final measurement.
Not only is having a full time job is hard to do woodworking, if you have a family as well, then that is another thing that you are going to have to juggle as well.  For me its a no brainer.  I always choose my family over my hobby of woodworking.  But when my family or job does not need my presence, that’s when I am free to let my brain just run loose on new ideas of what to build next.
Many beginners trying to get started in woodworking take one look at their budget and worry how they can afford to buy a whole shop full of power tools to get started. Fortunately, one doesn't have to spend a fortune to get started. There are really only seven woodworking tools that I would recommend any beginning woodworker have on hand from the start, and most are relatively inexpensive. However, with these seven tools, a beginner can tackle quite a number of projects.
What tools are needed to start woodworking? Well, this list can vary greatly depending on your budget. The best beginner woodworking tools are subjective but can vary largely depending on how much money you are willing or able to invest to start out in woodworking. It can also vary depending on if you are wanting to start out woodworking just as a hobby or as a side-hustle business. Most of the best beginner woodworking tools on this list are either tools I own, have owned, or at least have used in the past.
These YouTube videos provide great woodworking information that contains both traditional and modern methods. Each instructional video contains woodworking how to techniques to improve a woodworkers’ skills and also methods for how to work safe in the shop. If you want entertainment, then watch the video once. If you want learn, watch the again. If you want to master techniques and improve your woodworking skills, watch and study the videos repeatedly.
You’ll need a long screwdriver with a square blade that is very heavy duty. This gives you a lot of torque. You’ll also need a small and medium slot screwdriver. For working on cabinets or tight places in woodworking, you’ll need a screwdriver with a thin shank so that you can reach screws that are inside of deep holes. This is accomplished with a cabinet screwdriver. Get a couple of medium Phillips head screwdrivers, and a stubby one too, for those tight places. You may also want a ratcheting screwdriver.
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.
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