In my shop I use a large number of Jorgenson F-clamps. I use many of the small clamps, the most useful being the 12" version. Large F-clamps are essential for cinching down parts on bending forms. I also like aluminum bar clamps because they are much lighter than steel clamps, and therefore less likely to damage a carcase should you bang into the wood during a glue-up.
I looked around at many versions of Taiwanese drill presses. I ended up purchasing the Ridgid DP15501 15" drill press because I liked the way the quill stop was made, the work light, key storage, and the easy access to the belt change system. This machine was also on sale when I needed it, so that made it a slam dunk. Choose the one that suits you, as they’re all very similar. The table is large enough, and the distance to the column is large enough to allow you to do most anything a small shop needs.
My shop consists of a 9×16 storage building, with 3 feet being used for actual storage! I have a table saw, 13″ planer, lathe, sliding mitre saw, home made router table, small compressor, 5′ 4 drawer bench with vice, table top drill press, 6″ jointer, band saw, shop vac, wall mounted hand tool storage, clamp rack, power tool storage, and no room to turn around! But I put out a few nice pieces! Recently built, a 48″ entry table from 100 yr old milled poplar, coffee table from the same re milled red oak barnwood, and a little triangle shaped corner table from the left over red oak, a 7′ x48″ bookcase from old poplar, a small wall mounted poplar book case, and am presently working on a queen sized bed with a mixture of 100 yr old oak and new kiln dried oak, with drawbored pegging using black walnut from a tree from my yard! I’ve also made several mallets that I find useful from my firewood pile using Cherry, ash, hickory and white and red oak. Building anything in 108 sq ft is a challenge, but patience determination, and decent sales will make it work! One good point is that nothing is out of reach! Except maybe the bathroom!
You may want a garage door if you will need to access your shop with large workpieces or tools, or if you or future owners will ever want to use the space to park a vehicle. Garage doors are notoriously drafty, however, so if you think you can live without one you will probably be warmer. Instead, you could opt for out-swinging double doors. In a small shop you can, at a pinch, rip longer lengths of lumber by feeding the material out of either a strategically placed door or window.