I have done everything without cheats or trainers or
anything
100% progress
All 6 girlfriends at 100%
All golds in all schools
All gang territories taken over
All skills maxed out
Both Beat the Cock challenges done
Burglary done - infinite sprint
Gambling skill level Whale - maximum wager is $1, 000, 000 and you can borrow up to $1, 000, 000 from a casino
I have done everything without cheats or trainers or
anything
100% progress, I think
~$132 million
All golds in every school
5 girlfriends at 100 percent (i killed millie to get that security card)
weapons: knife, desert eagle, combat shotgun, SMG, m4, grenades, minigun
All skills maxed out
All gang territories captured
Better save file I have finished the game 100% again and now the save is better:
Both Beat the Cock races done
All 6 girlfriends at 100% (unlike the old save where Millie was dead)
Gambling skill maxed out - it was zero in the old save file
Although now you have only 6 million $ instead of the 132 million from the old save, it should be enough. If you want more just go to the betting shop in Montgomery or under the Mullholland Intersection and bet all the money on the horse with the highest odds.
Awaiting approval.