I eventually found my way to Into the Odd by way of Cairn, which is Yochai Gal's mash-up of ItO and Knave by Ben Milton. Cairn, like Knave, is classless and species-less, where your character is defined only through roleplay and your choice of gear, which is limited to ten inventory slots. Cairn is designed around forest-based dungeon-crawling, which I find refreshing. I believe I read somewhere that Gal's initial idea was to use ItO's system to play in Necrotic Gnome's awesome-looking Dolmenwood setting. I was also considering using that for future games, but at that time the Dolmenwood stuff was still "in development." It is meant to be used with Old School Essentials (also by Necrotic Gnome), one of the more popular commercial OSR rulesets currently available but not one I wanted to fool with.
I tried very, very hard to stick to Cairn. I liked it a lot. Eventually, however, I gave into temptation and went to see what else Into the Odd might have to offer. While Cairn takes all of the best bits of ItO, I started thinking the stuff from Knave wasn't absolutely necessary. ItO's five-minute character generation with none of the usual choices to agonize over was appealing, as was its nebulous mix of urban and subterranean adventure.
A Quick How-To for Creating Characters in Into the Odd
Roll 3d6 three times and assign the values, in order, to the three attributes: Strength, Dexterity, and Willpower. Roll 1d6 for HP (which interestingly is NOT hit points, but rather hit protection). Cross-reference your highest attribute value with your HP on a table to get your equipment and maybe an ability or defect. Slap a name on it, and you're done. Seriously, that's it. Character generation needs to be this simple, because the fact is, your characters die fairly easily. You can use your wits and common sense to minimize the dangers of adventuring, but if you continue to press your luck, sooner or later that luck will run out. Lethality is a big part of OSR games in general.
Attacks just automatically hit in Into the Odd...every time. Your hit protection is a reflection of your self-defense skills, and if you don't put your opponent down quickly, they will wear you down and eventually hurt or kill you. Go toe-to-toe with something a lot bigger and faster than you, and no amount of skill will save you. The only rolls in the game are damage rolls, attribute-based saving throws, and the very occasional luck roll for when success or failure actually does just come down to chance. I like this simplicity and minimal number of die rolls because of all the many, many times that freakishly bad rolls in other games made my character depressingly ineffective.