steeldragons
Steeliest of the dragons
1. steeldragons -- re: money roll. No, don't split the difference. Roll for the class that gives you the most and ignore the others, so 5d4X10gp in this case.
Coolio. This is the kind of thing that comes out of years of houserules vs./masquerading as "by the book" knowledge in ye olde mellon.

2. If you don't like the secondary skill roll, roll again, or just choose one.
No, this is fine. I like the challenge of figuring out how to make things work/fit into the background. I'm figuring for this chap, that he is trained in the making and operation of boats but is not fond of the water. "I can make 'em. But don't 'spect me to get in one!" I'm figuring, he can basically "doggie-paddle" (i.e. won't drown!) but he's not a "swimmer" in any adept sense. Maybe even a lil'/minor/pseudo phobia.

Neither here nor there but when I was rolling for this guy, I realized I hadn't rolled for Shiyana (in the Alpha game). Ironically, it came up as an 80-something indicating "No measurable second skill." So, she still doesn't have/apparently didn't need one. haha.
3. Weapon Proficiencies -- like money, you take the most favorable class and go with it. In your case, again, you'll have fighter proficiencies and will gain more when your fighter level indicates, without regard to your thief level. But you still get double damage when you backstab, even if it's with a weapon that a thief can't normally use.
Right. Ok, cool. Again the memory v. book knowledge on the fritz.
4. There are 3 'breeds' of halfling: Tallfelllow, Hairfoot, & Stout. So, no, a Hairfoot is not a Stout. Hairfoots ["That's HairFEET!"] are the most common halflings and form the baseline for the race.
Yes. I thought I knew/remembered that. But then got fuzzy reading the halfling race description for special abilities and there was something that "Stouts" got the others didn't. I'm definitely a hairfoot (FEETS!). But wasn't really clear on what the Greyhawk default halfling was.
Thanks for the clarifications.
As for the "Anti-hero" style game...until you wrote that, I was planning on making him Neutral Good, then read your post and recalled Thieves can't be "Good".We always had it can't be "Lawful" instead (reasoning anyone can steal things, but even evil societies don't like people taking what's not theres!). Again, houserule/book rule conflama of the brain.
The AD&D-Force was clearly weak with me yesterday! lol.
Though I am not a fan of "evil" campaigns/playng the villain (accidental/wrongly accused villain works just fine).
But for the "Scrappy-Doo" gambler/good times self-perceived "ladies' halfling" ragamuffin I was beginning to form him as, a straight Neutral or even Chaotic Neutral (not to worry, fellow Players, that does not, to me, equal "Chaotic Nuts"!) would work just as well.
I could totally see him in a "forced/accidentally falling into the hero [or villain]" role and/or "redeeming" to actually think of others as much as himself...well, not as much, but close.

So works for me if it works for everyone else. (In case it hasn't yet become evident, I'm pretty easy to please.)

--SD
PS: Are halflings called "Hin" in Greyhawk or is that Mystara? What do they refer to themselves as?