Aaron, I will give you some tips on how I progressed through handstands. For the last 4-5 months I trained handstands exclusively stomach to wall, 3-4 times a week. The big things I focused on was 1) keeping the weight centered on my palms. 2) keep my arms locked, and keeping my elbows turned inward. This is was simply rotating my elbows towards my ears while inverted. I find I am stronger in this position. I do this as well with the planche and find the carry-over to be tremendous. 3) Keeping my stomach hollowed out. 4) Keeping my glutes and legs locked, and toes pointing up.
I basically worked up 60 seconds each session. Now I follow a MWF routine. Day 1- I work HSPU, I do them off of homemade p-bars. I am working on progressing toward head-to-floor full ROM. Day 2- I do a stomach to wall holds. I bring my legs from straight up to straddle and back up 3 sets of 5. I use as little support from my big toe as possible. I find this has really helped as most sets I come off the wall for a freestanding handstand. Day 3- I do wall taps. So still static hold work, but just a different drill. I have yet to determine a time duration or sets and reps for it, coach sommer recommends his athletes build up to 10 minutes straight. I am probably thinking 5-6 sets of 10 reps.
I find this helps keep the routine fresh and still allows me to progress in strength. The other day I completed a 15 ft. freestanding handstand walk.
Hope this helps