Cordless drill (the first one I had was one of the first, a Skill. It didn't have a readily removable/replaceable battery, but I did buy and install a replacement at one point. That tool finally died.)
Cordless screwdriver (I like the Black and Deckers, cheap but their stupid Versapak batteries are expensive. Still, as long as the batteries are good, they are handy tools).
My grinder, which believe it or not, I made myself from a a motor that came from a dryer and parts I bought. I also adapted that to make a table saw!
Circle saw (Porter Cable Saw Boss, it's compact, light, not a cheapie, but does 90+% of what a bigger/heavier circle saw will do).
Dremel (yeah, from time to time you'll be glad you got one).
Jigsaw
Orbital sander (Makita) and belt sander (Porter Cable).
Manual stapler with adjustable spring-applied tension. I have a couple that use anywhere from 1/4" to 9/16" staples. I use those staplers pretty frequently, keep 1/4" staples in one, generally 1/2" in the other.
Miter box
Level
Square
Tool bucket
Tool belts
Head lamp with rechargable batteries!
My trusty every-day-carry mini flashlights with rechargable AAA battery!
Knee pads and a variety of gloves
A variety of solvents, including a gallon of acetone (pour them off into smaller containers)
Ear protection (the kind that look like big headphones). Slap them on your head when using electric tools that make a lot of noise or are otherwise generating ear splitting noise, e.g. with a hammer. Don't mess up your ears.
Multimeters, even the cheapies at Harbor Freight, are a must for the DIY inclined.
A variety of soldering equipment including a propane torch and iron.
Porter Cable 382 5" Random Orbit Sander
Although... does a workbench technically count as a tool?
One day I spotted a desk someone had put out on the curb and brought it home in my station wagon. I converted it into a workbench by jury rigging leg extensions onto it. It has several great easy-slide drawers. I added a lower shelf between the legs (on which sit most of my portable power tools), installed a tough veneer top, bench vise and wood vise, have shelves extending upward from the back edge. My homemade bench grinder sits on it and it has a couple of swivel lamps on either side, the kind you see in Pixar film credits. It's sweet, and sits in my tool room. It's solid as a rock. I don't think I could buy a better workbench anywhere.
One of the biggest advantages of being a Tool and Diemaker I guess is if I don't own something, the shop has something I can borrow, or one of the other guys owns one
Yeah, that would work. I'm less than a two minute bicycle ride from my town's tool lending library. I hit them up occasionally.
Which reminds me...taps and dies are epic to have.
I use my taps (complete set) frequently, but have just an 8-32 die. I have used it many times, however. I've made a lot of bolts out of nails! May get a die set someday, just haven't seen the deal I like.
Any recommendations on the digital calipers mentioned above?
Harbor Freight often has them for real cheap (IIRC, something like 7 bucks), that's where I got mine. I use it once in a while, is reasonably accurate for my general usage, you can zero the thing quick.
I have somehow managed to live without wire strippers all my life and I really feel I need to invest in them. Ran a new 20a circuit last week and it was a PITA using a knife to nick the insulation.
I waited a really long time before I bought my wire stripper, until I finally saw one I liked. It's had a lot of use. It's a cheapie, strips various size insulated wires, also cuts and you can clean threads of smallish bolts with it.