20 Questions Tiiiiiiiiime

1. Ability scores generation method? - 3D6 in order. If you get the required stats, you can then be a demihuman. If you don't, you're a human and you can move the stats around as much as you want.
2. How are death and dying handled? - If you hit 0 hitpoints, you die. I have been thinking about introducing a rule where you get an additional Save vs. Death to see if you go into a coma or something like that.
3. What about raising the dead? - Extremely high level clerics may do this for a truly outrageous amount of money or if the party agrees to do something very dangerous for the church. You'd have to find access to one of these clerics though.
4. How are replacement PCs handled? - Either one of the retainers is promoted or you roll up a first level character. There's almost always somebody hanging around that's worth being "promoted" though.
5. Initiative: individual, group, or something else? - Group. Somehow it adds an extra bit of flair to combat because when I ask the party to roll, everybody rushes to be the one to roll it or briefly argues about who has had the best luck at it recently.
6. Are there critical hits and fumbles? How do they work? - Roll a 20, it's a critical hit. Either the damage gets multiplied or something extremely advantageous happens (generally if somebody rolls low on their damage, rather than multiplying it, they'll disarm/temporarily blind/hamstring the opponent). Rolling a 1 is a critical miss and generally leads to people dropping their swords, breaking their arrow strings, etc.
7. Do I get any benefits for wearing a helmet? - Everybody wearing armor is assumed to have a helmet of some kind.
8. Can I hurt my friends if I fire into melee or do something similarly silly? - Oh my yes. If you roll a 4 or below, you get to roll another attack against your fellow party member.
9. Will we need to run from some encounters, or will we be able to kill everything? - It is generally advised that the party have a Plan A, Plan B and probably a Plan C for every encounter. Discretion is the better part of valor. So yeah, you're gonna have to run a bunch.
10. Level-draining monsters: yes or no? - I'd like to say yes; I typically will go to some lengths to avoid stocking them, so in practice, no.
11. Are there going to be cases where a failed save results in PC death? - Yes. Hasn't happened yet, although there's been one close call with a poison needle.
12. How strictly are encumbrance & resources tracked? - Resources are tracked fairly rigorously, encumbrance hardly at all. I've basically said "don't do anything outrageous or I'll get really picky about it" and that seems to have done the job in terms of everybody keeping things reasonable. There's a fair amount of hiring of retainers and they've bought donkeys and carts as well without needing to do a full accounting of everything in everybody's pack, which is good.
13. What's required when my PC gains a level? Training? Do I get new spells automatically? Can it happen in the middle of an adventure, or do I have to wait for down time? - It has to happen between sessions. There's no training involved. Clerics automatically gain spells going up levels, mages don't.
14. What do I get experience for? - Surviving/doing well with encounters, 1:1 for money and non-magical items looted. Oh, and we use Jeff's Carousing System.
15. How are traps located? Description, dice rolling, or some combination? - If the player says they search an area, there's a description. If they don't, there's dice rolling.
16. Are retainers encouraged and how does morale work? - Retainers are very much encouraged, although they do tend to lose morale when openly referred to as "meatshields". Morale is I roll 2D6 and make stuff up based on my reading of the situation when I feel it's appropriate.
17. How do I identify magic items? - Detect magic is a good starting point, allowing you to "read auras". More specific information requires more intense study/use of special rituals.
18. Can I buy magic items? Oh, come on: how about just potions? - No and mostly no. You can buy stuff like "love potions" and other alchemical nightmares with the caveat that they tend to be made by people who sample their own wares on a regular basis.
19. Can I create magic items? - In theory. We'll find out when we get there. I'll know when that is.
20. What about splitting the party? - It's your funeral. It does mean that I get to physically separate the players by making them go into different rooms and then run between them as they try and figure out what's going on. This can be really fun.