I'm coming off of an HD EG onto a Valkyrie Interstate. I really can't see me ever going back to Harley. I have had six Harleys and to be perfectly honest they have all been far less reliable than they should have been. Five of the six have left me stranded at some point. This is my third "wing" and I have never been stranded on a wing. Not to say that it couldn't happen but, my experience and that of every rider I know is the same. For serious long distance the wing/valkyrie is superior. The most reliable Harley we ever had at our house was a 2001, 883 Hugger that my wife owned and the only issue it ever had was oil leaking from the rocker box seals when it was a year old. My 2001 1200C broke down in the lot of a Biscuitville when it had 750 miles on the odometer. Burned out voltage regulator. This is not to trash HD. I love their bikes a lot but, I like coming home on the bike and not in a U-Haul, a rollback or a trailer, which I have done way more than I should and all on HDs. I refused to take my electraglide on a long trip because I knew it would leave me stranded at some point.
The clutch issue is probably a neglected master/slave cylinder. That's not a complicated fix even if they need a rebuild.