I've made or seen a lot of hand-made stuff:
My mom made these for me, when I started gaming:
leather 2 book binder, to look like a big spell tome (kept PH & DMG in it)
leather pencil case, to look like a scroll case
leather dice pouch, to look like a leather pouch
I've made more stuff:
miniature campfire, to represent where the campfire is, relative to the PCs for when the DM ambushes the party
miniature bar, to put in the tavern outline on the battlemat, for those bar fights
miniature canoes, for when our party was traveling down a river in the arctic (summer time)
gaming platform to go on top of normal table (3 foot square, with legs to raise it above the table, giving space for books and drinks on the normal table, and the map with minis go on the platform, gives much more space, but was a little too tall. Put out of service, and turned into a multi-layer shelf for my wife's art projects that needed to lay flat and were not small. If I were going to rebuild it, I'd make it so it had 6" clearance on the base table, not much more than that is needed, lest it be too high, and hard to reach the upper deck to use it.
wooden dragon for a big boss fight, before I had minis for that. It was a pine board, with a dragon drawn on the side, cut out the silouette, painted, and it was basically a long skinny dragon (which fit for the custom wingless/flightless dragon it was anyway).
wooden block minis for the DM to represent hordes of enemies. Once again, made in my high school wood shop days, before we had access to minis.
I've also made a castle, houses, hills, forest for other minis games. I've got my own wood shop now, so it's pretty easy to whip up stuff.
Electronic stuff I've made:
Modular 2e character sheet for Word Perfect (that was a long time ago). I had a page made for each topic, general, skills, combat, items, spells, and one per class (including XP table, THAC0, saves, etc). You copy the file and rename it to your PC name, and then delete the pages that didn't apply. The combat page was nice, it was meant to hold the stats for your weapons and armor (in various configurations), so you always knew your THAC0 for any weapon, and such. It also had a big space for HP math, rather than trying to fit it into a worn out box on the front of the char sheet. We tended to not use this style, after 3E, as we got into using other tools.
Apple Basic 2e monster encounter generator: it had 2 modes, one for entering in new monster stats, the other mode for creating encounter blocks (the pre-cursor to stat blocks). You'd type in the name of the monster, then how many you wanted in the encounter. It would then print (on paper) the basic stats THAC0, AC, attacks, specials, and then the HP total (rolled randomly) with little circles to cross out points, in 5 point blocks. Each monster was it's own line. 7 goblins might look like:
Goblins (3)
AC: 7
THAC0: 19
Attack: shortsword 1d6
Specials: none
HP: 6 ooooo o
HP: 4 oooo
HP: 5 ooooo
As a GM, you'd run the program, and make it dump out a ton of encounters that you'd need
Apple Basic Dungeon mapper: a lo-res drawing tool to carve out a dungeon. Each color meant something (40x24 pixels, and 16 colors to pick, map started filled with solid brown for dirt).
When you printed it, I'd swap out each color pixel for a 2x2 character meant to represent the content. black was open, brown was solid and printed as:
##
##
Apple Basic Treasure Roller: i put in all the 2e DMG treasure tables. As a DM, you'd type in the treasure code (letters), and it would roll them up, and print them out.
I did all the Apple basic stuff in high school. It's what I had at the time. The DM had an apple at home, so he could run these and get what he needed for writing adventures.
Looking back at the software I whipped up, it was pretty easy to run 2e with that stuff, and with a bit more work we could have wired more parts together, like making the monster tool roll up treasure for itself, and making a random encounter generator, to then roll up monsters.
Stuff I've seen:
Dice rolling tower: put your dice in the top, it tumbles inside, and comes out on the bottom into a little receptacle. saves space, and keeps the die from going all over the table. Also ensures a fairly consistent random roll, rather than the dead plop roll some players try to get away with to cheat.
Dice Rolling Pit: a friend made this (used it in the car to game on the drive to see me, 1500 miles). Basically a small box, about a foot square, 3" deep (made with flooring samples). Roll your dice into it, and they don't bounce out, and they tend to land flat, rather than cocked.
