I'm not familiar with the FT piston & the replacements available. Most folks want to raise the compression when they replace a piston. From what I hear, that is the main performance modification that FT's respond to the best, aside from a performance camshaft.
Do these replacement pistons have enough material in the top of the piston to machine the dome down or off completely?
As long as your starter has been maintaned regularly, you have a strong battery & you remember to prime the engine well prior to starting, you shouldn't experience much problem. I believe that the main trick to extending starter life on the FT, is having a good tune on the engine so it starts promptly. Prior to starting, I always rotate my throttle 4-5 times to operate the accelerator pump in the carb. This shoots a squirt of raw fuel into the intake tract with each twist of the throttle, providing a nice rich starting mixture & the bike fires right up without excessive cranking of the starter. Avoid the over cranking & your starter will last.
Good luck & please let us know what you find out.
J.
PS. You will gain some compression from the over bore even if you use a flat top piston. Embrace it, compression is not the enemy, poor fuel quality is.