I have a '95 FXSTS, seems to shift hard (sometimes) from 1st to 2nd then gets easier as I shift up? Is tis a sign of a needed adjustment?

 

Possibly. Try adjusting the clutch, which may improve the change a little.

 

It could be your clutch yea. You would probably know if it is your clutch if your bike tries to move a bit when you have it in gear and the clutch pulled in.

I have a new 2014 Breakout and it clunks HARD. I wouldn't read too much into the clunking.