Sorry to hear your going through so much hassle with the motors. A buddy went through 3 motors on his 07 110, on the third he just traded it in for a new roadking. His experiences of blown motors was about the same mileage as you have and he is not a heavy handed rider, just a cruiser. You might look at upgrading the engine with something other than HD parts. If you going to be out of pocket so be it, but then put S&S inside or go to a low compression 124 with all the right parts inside it and ride on.
S&S replacement crank, Timken bearing, s&s or other pistons, lifters, blue cam plate, pump, tapered pushrods, use existing heads, but after 50k would send them out to either be worked on or refreshed.
You can use your cases and stay 110 or even go to 124, but you may want to just drop in a motor and be done. Just remember to upgrade the throttlebody and clutch if you go that route.