If you bore your existing cylinder and just buy the pistons and rings it may be more cost efficient if you can do the work yourself.
If you bore your cylinders you may want to just do a 106 inch which will leave you with a little thicker cylinder walls which would be better for handling the heat.
Doing the top end is a easy DIY so if you have the basic hand tools and some mechanical ability you can do the work yourself. The only specialty tools needed is a torque wrench, I use a $2 hose clamp to compress the rings.
You should get a 100,000 miles plus on your engine right now so you got a lot of time.
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08 FLTR candy red sunglo,with 2015 103 HO, V&H Dresser Duals with Monster Rounds, Power Vision tuner, Willy Shiny Wheels and Forks and a bunch of other stuff.