Let’s talk about what you find crucial for your toolbox: Favorite Tool(s): This is a hard one. If I had to sell the majority of what I own and just keep a few key pieces I would go with the following:

• Pancake Compressor Kit w/ Brad-Nail/Narrow Crown Staple/Finishing guns: If I had to go back to hammering rotten little finishing nails with a tack hammer…I think I’d give up woodworking and take up knitting. The time savings alone is enough to make me a little wobbly in my knees when I think about it. A good combo kit can be picked up for around $200 and will include everything you need to get started, up to and including the nails/staples themselves. So, apart from the time savings and the obvious cool factor of walking around with something vaguely gun-shaped…think about never bending finicky little nails, missing the nail and hitting your thumb, or worse yet the piece of furniture you’ve been working on all weekend. Think about never having to dig around in 2 inches of sawdust to find that evil little brad-nail that you just dropped.
• Table Saw: Any woodworker worth their salt already has one, or is shopping for one, the exception being those that simply don’t have the room for it. I love my ugly orange screamer. It makes too much noise. It makes too much of a mess. It’s a little scary…I love it. The common problem many people have, is that they think of the table saw as a weapon that’s pointed right at them. Which isn’t necessarily wrong. However, there’s so much you can do with one beyond just ripping down wood into manageable lengths/widths. I use mine to make Dado’s, I’ve used it to smooth out and trim the faintest little bit of paint off the edge of a shelf. I’ve even seen some older woodworkers use them as a lathe and round out stacks of 2×4’s (do that one at your own risk). It is the single busiest tool in my shop.
• Clamps: Bar. C-shaped. Ratcheting. Vise. Get as many as you can as often as possible and don’t cheap out. All plastic bodies…fine. But make sure the guts of that clamp aren’t all plastic as well. There will be very few moments in your woodworking life when you don’t require a clamp for something. Be it for holding two pieces of wood together for a glue-up, squeezing a joint together that’s slightly out of line, holding your piece to the workbench as you sand or router the top and/or edges or holding down a straightedge to run your circular or jig-saw against…..the applications and uses are endless!