Is it ALWAYS the shift from first to second gear, or does it happen shifting to any gear? Always on an upshift, or does it hang on downshifts as well? Is it worse or better when cold, or no difference?

 

It can happen in any gear .
Not near as often but sometimes it is hard to downshift.
At first it mainly happen when cold going from 1st to 2nd then went randomly to any gear. Only gear I don't remember it happening in is 4th.
Cold or hot doesn't seem to matter.
I adjusted the clutch a couple days ago and went on about a 25 mi ride which included in town riding and did not have any problems but felt that on downshifting a couple times it was a little hard. Might have been just me though.

 

This is where I would check … your problems sounds like the spring plate …

 

FlhChaz nailed it.
After I had an indy put a new stator in and him telling me that I needed a clutch sooner than later I finally broke down and bought an energy one extra clutch plate kit and put it in this weekend.
Everything was going great until I got to the spring plate, well actually the spring plate came out ok then I was having a heck of a time getting the next plate to come out, got to looking and the basket was littered with the little brass things holding the spring plate together.
Finally got all those dug out and things went smooth from there. Backed her out of the shop fired her up and was totally amazed at how smooth she shifted into first. That hadn't been a problem before but man , it was really nice now. Took her for a short spin and I knew my problem was solved.
What I really don't understand is why the mother ship would spend all that time and money building a spring plate when just adding another friction and steel to the clutch pack would have been a whole lot cheaper and in my opinion a whole lot better setup.
Anyways thank all you guys for the input. Some of your suggestions got me to checking and fixing things that would otherwise have caused bigger problems down the road.

 

Glad you got it fixed and thank you for coming back and telling us what the fix was.