The GI Bill cannot be used for your Private cert. It can be used for any Part 141 cert or rating after that. With that said, all your training under Part 141 GI Bill covers 60%, which you front the money and after the cert/rating they will repay you. Now, that was under the old bill, not sure about the new one MGIB. As far as equip, talk with your flight instructor and other students, get their opinions for what works with the type of equip flown.
Good Luck with your endeavor, enjoy, and ask questions.