Back from a game of S&I with GraveBot. Apparently, my friend was hosting a listenserver (non-steam) via LAN, and the game crashed twice in about 1h30mins. I freshly installed HL on both computers and the only modification I made to the mod was just adding the bots. There were a total of 22 bots + 2 players. It seemed to crash during intense combat. I haven't tried playing with less bots yet, so I'll keep you updated to see what happens.
(RE: Answer 3: So you mean you haven't implented that yet? I read something about that on your bot guide, so I assumed you added it in already.
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