Another option for you just occurred to me, that you might consider.
After you have your load development done and you have your selected load in hand, one huge component of the time spent reloading is case preparation. The tools for case prep are quite inexpensive. You could buy the case prep tools, do the prep work yourself, then buy the components and have your buddy do the actual reloading for you. That would limit how much time he actually has to spend pressing your rounds (especially if he has a properly set up turret or progressive press). Saves you the expense of buying all of the reloading kit, saves him the time of handling all of your brass.
To do your case prep, you'd need:
Lee hand press - $50
Lee Universal decapping die - $12
Case tumbler or ultrasonic cleaner - $55-110 for entry level
Media or cleaning solution - miniscule cost per batch of brass cleaned
Lee COAL gauges - $10 or less
Lee Cutter and lock-stud - $10 or less
Lee Chamfer tool - $4
Combo neck brush - $10
Primer pocket cleaner - $10
That investment of $160-200 would let you do everything you'd need to do to get your brass ready to hand him clean, deprimed brass, bullets, primers, and powder, and let him start cranking out rounds straight away.