First thing: Get him on this forum to interact with this advice instead of relaying messages.

Secondly: Well I just moved from .5/1 to 1/2 on Party Poker after ~10k hands of 2BB/100 (mostly without PT and a HUD). After getting a few thousand hands in at 1/2 and ~3BB/100 and PT/HUD I quickly jumped to 2/4. After initially having great success at 2/4 I fell back to even. So I'm back at 1/2 now and actually spending some time trying to analyze why my play yields what it does instead of just winning and moving up once I feel comftorable with the bankroll.

My point- Does he want to invest the time to figure out how to move up? Probably not if he's fine playing 100k hands at .50/1 and has you pushing him and figuring out his problems.

Should he move back to .50/1 to make back his money? Investing the 25 to get Pokerace HUD and keeping his style at 1/2 on party poker he should have no problem making his money back there. I've only played limit on Party Poker and I think anybody should be able to profit there with a little effort. Making $500 back will take him 28k hands at .5/1 at his rate. I bet he could make that back a lot more quickly at 1/2. Or even by getting a job at Wal-Mart. (They'll even pay for your lunch break lunch break now)