What should I start with for hand planes and chisels?

For planes, a No. 4 smoothing plane or a No. 5 jack plane is a good first choice. A No. 4 is handy for smaller pieces and final smoothing, while a No. 5 is more of an all-rounder for sizing and flattening stock. You don’t need a full set right away. Add longer planes or specialty planes once a project gives you a reason.

A sound vintage plane can be good value, but check that it isn’t cracked, badly pitted around the blade seat, or missing parts. A decent modern plane is also an option if you’d rather spend less time sorting out condition. Either way, budget some time for setup.

Keep the chisel kit small at first. A quarter-inch, half-inch, and one-inch chisel cover a lot of common work, though the sizes you reach for depend on what you plan to build. A few good chisels are more useful than a large set you have to maintain.

On sharpening, a guide can help you repeat an angle, but a tiny amount of skew isn’t automatically a problem. It matters more when you’re trimming a square shoulder or chopping a mortise. Make sure the cutting edge is sharp across its width and that the back is flat near the edge. A 1200-grit finish with a strop can be usable; if the edge is damaged or still struggles to cut cleanly, go back to a coarser abrasive before refining it.

Don’t let sharpening turn into a separate hobby unless you want it to. Pick a sharpening setup you’ll actually use, learn to raise and remove a burr, and test the edge on wood. Clean, controlled cuts matter more than getting a mirror finish or shaving arm hair.

Also, what you’re making should guide the purchases. A small furniture project and a large workbench don’t ask the same things of your planes. Start with one versatile bench plane and a few chisels, then fill gaps as they show up.