what would be the best way to spend $300?

[Brian Holcombe]

I share Prashun's sentiment. Save your money until you know where it best applies.

Sell the table saw anyways. I've hurt myself with hand tools (a few times) so caution needs to be applied to all things from handling rough stock on through to finishing.

As a relative newbie, it's a good idea to do box making. You can also just cut joinery for practice.

Given that you have a planer, I would remove the wind (twist) from a board before planing. My normal procedure is to rough cut to length, joint (remove twist/bow/cup from one face), transfer my thickness marks with a gauge and then cut the opposing face to thickness). A thickness planer does that last step for you.

[Mark Fisher]

I am only a few projects ahead of you, but here is what I learned. Stick to two planes.....a jack and a low angle block plane. Learn how to sharpen them so you can shave hair from your arm easily....only then consider other planes. This may mean investing in a good set of stones. Do it. Second, get good, accurate marking and measuring tools. A machinist's square (Amazon, McMaster Carr, not adjustable), a marking knife (small Opinel folding knife works except for dovetails), a cheap digital caliper (Harbor Freight is fine), a decent mark gauge (Tite-Mark was my splurge and I don't regret it....pin or blade is fine). Third get a dovetail and tenon saw.....old Disston or similar is fine and learn to sharpen it. Same with panel saws ex. cross cut and rip. Restoring old tools is fun and teaches some primary woodworking skills. Next, make some bench tools like a shooting board and bench hooks. They teach you to make things accurately yet are pretty simple. Make them perfect. Finally, clamps. You can't have enough of them and cheap nasty ones are cheap and nasty. If you have a bench and it is thick enough, get the Gramercy holdfasts. Handy, cheap, convenient and very fun to use. BTW - I learned to hate my table saw so much it will be out on the curb next week minus the blade, motor and fence.....I'll sell those bits!