@Somatic: Cleared it on 1999 mode. Apart from that 2nd Handyman fight it was mostly easier than my first play through on Hard. There is a condition though:|
This game - especially on 1999 mode - gives you the chance to fuck yourself by paying for a revive. If you instead reload the last checkpoint and keep your money, you can upgrade like crazy. By the end of the game I had fully upgraded Crow, Charge, Possession, Return and Bronco, and on top of that I had fully upgraded the Volley gun, RPG, shotgun and machine gun. In short, I was absolutely unstoppable.
I think that 2nd Handyman in Finkton is the last spike to overcome. After that it's plain sailing, so maybe consider giving it another shot some time? Also, for the record, I'm not a very skillful FPS player. Need any advice, just ask...