It's pretty much impossible for the trans fluid to leak into the primary. I would say that with 2K on the bike there shouldn't be any leaks and I see no reason for you to shy away from this bike. You can always buy the extended warranty if it makes you more comfortable.
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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.