2. Just the basics—I’ve used a compound miter saw, circular saw, jigsaw, band saw, router, table saw, drill, finishing sander, belt sander, Dremel, oscillating multi-tool, bar clamps, and a Shop-Vac. I haven’t used a planer, jointer, or lathe. I’ve never owned a table saw but have used a circular saw or improvised with a router for a few long cuts.
Do you enjoy woodworking?  Do you have a budget that you have set aside just for your woodworking?  If you are not a millionaire, than more than likely you will have some sort of a budget.  Let me give you a little insight into why you are here and what you will find on this site.  Do you enjoy woodworking as a hobby, part-time job or side job, or a full time job?  Or maybe you are wanting to turn your hobby into a full time job.  If that sounds like you than  your in the right place.
Another staple in the beginner woodworkers tool kit has to be the cordless drill. Used for either drilling holes or driving fasteners, this tool gets used on almost every project. There a tons of options here regarding size of batteries, aka power, but something around the 18-20 volt range is a good all-around size that will not leave you constantly wishing you had something larger or smaller. Here is a large accessory kit at a good price that should give you most of the drivers a bits you will need.

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These basics are going to set you back about $180, leaving you with $320 left to work with.  We are going to be leaving behind two hand powered tools from the $250 shop and upgrading to powered alternatives.  This should lead to more consistent results, more enjoyable builds, and increased efficiency.  These are all goods things that only the biggest fans of The Woodwright's Shop would argue with.
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.
If you are an advanced woodworker then you might want to check out the Wood Whisperer channel. It has advanced projects broken down to the details in multi-part series and also technique videos. Mark Spagnuolo has been creating DIY woodworking videos on the channel since 2006, so there is a lot of content to scratch the itch of any woodworking enthusiast.
To get the most out of your router, you are going to want a router table.  You may find yourself asking if you really need one - if you do, check this post out.​  It's one of those purchases that you won't truly understand how valuable it is until you have one.  Given the budget of $2,500, I'd suggest looking at the Bosch RA1171 ($150).  If you want to see our favorite tables along with write-ups, check them out here.
The solution to potentially wedged boards on a jointer is to add a planer to the mix.  A planer has a flat surface with a cutting edge that is exactly 180 degrees to the surface.  This allows you to position the jointed edge flat on the planers surface and make a cut to the opposite side of the board that is perfectly square.  As an added bonus, the planer allows you incredible control over the thickness of the boards you're planing.  ​
Not many YouTube woodworking channels are run by guys who also happen to have PhD’s in medicinal chemistry, but this one is. Brian Grella’s channel offers a mix between more atmospheric videos that aren’t heavy on explanations (as the one shown above), and ones that are firmly in how-to territory, like this one for making a beautiful wooden bowl using nothing but a router and a drill press (no lathe required):
If I had it to do over again, I would stick to an entry level miter saw and table saw until I had both the funds and need to upgrade to more capable saws.  Because of this, I'd stick to the two saws we looked at in the $500 build: ​The Craftsman Table Saw for ~$150 and Hitachi 10 inch Miter Saw for ~110.  These two additions bring our running total to just over $500.  
The next important hand tool for the woodworker is an accurate tape measure. Get a retractable one that is at least 25 feet long. Any longer than that, and you start having problems getting it to roll back up. Since measurements on large scale projects can be very susceptible to even the most minute measurement variations, you’ll want to make sure the “hook” or tab at the end of the is firmly attached, with no give. When they get loose, you’ll have as much as 1/8” variation in your measurements. This can add up to some severe accuracy problems in the long run.
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