I've done it half a dozen times ... The hardest part is lifting the tranny out of the cockpit without herniating oneself. ERA has to come out from the top. I find that a deep sumo-like grunt works best. Or like the jet jocks do to keep from passing out when pulling g's
Once that is done, then you can go underneath for the bell-housing, clutch, and flywheel. Stick a screwdriver in the starter bolt hole and through a hole in the flywheel to hold it still while you unbolt it.
I don't remember if we discussed this in a phone call, but Tilton had me take my Tilton Super Starter housing to a machine shop and have them take .060" off the face of it (the face that mates to the block plate/bell housing). That was the only way it would allow the pinion gear to engage the ring gear enough to meet the Tilton spec. Sort of a negative shim. If you are having similar "mis-engagement" that would eat the ring gear up.
Check the pilot bushing and see if it looks ok as you install the new flywheel. Some people say use new bolts every time. I don't, but I do use Red Loctite. Use the screwdriver again to hold it while you torque the bolts. ARP bolts don't use washers. And McLeod Alum F/W have steel bushings in the bolt holes so you can torque 'em good ...
Good luck!
Sam