Alright, I'll give some advice.
Are you in it for the money only? If so..This conversation is over. I like to gamble too, but I like improving much more than gambling.
Are you in it to improve? Then start off spotting him a ball on your break, and play for whatever he feels COMFORTABLE playing for. Don't push the bet. Trying to jack the bet when you are ROBBING, and when BOTH you and your opponent deep down KNOW you are robbing, is just gonna piss the guy off and he will just quit playing you.
I used to play with a guy all the time in the pool hall I frequented back in WA. He offered to play $5 One Pocket, and I accepted, because he could play a little and I just wanted some heat on my game.
I got about $15 in his pocket, no big deal..Kept the game friendly, laughing, joking, whatnot.
He bumped the bet to $10, and I started focusing..He got down few more games, and I offered him the breaks to even out the game a little, as he was getting beat by a lot of balls, but was also struggling with his shotmaking.
We got up to $60 a game by the end of the night. It NEVER would have got that high if I was just content to rob him.
I got myself in dead stroke for like 4 hours because I made the game EVRY challenging. it would not have happened if I just tried to barely win every game, in order to keep from having to spot him.
Russ