Harley stuff is great. After market stuff can be better, but alot more $$$. My rims are the option for 2005 from HD. They are spoke front end is a 19. Check ebay for either sportster 21" rim or dyna 19". The street bob has a 41 mm front end ours has a 39 mm front. It may work but dont hold me to that. The rear, to my understanding, wont fit as the newer dynas have a wider swingarm. The bearing issue isnt hard. HD dealer can replace one with the other.

 

According to a search of catalogs:

19" front:
'00 - Later XL (except '11 XL1200C, XL1200X, and '11 XL883L)
'00 - '05 Dyna models (except FXDWG)

16" rear
'00 - later XL (except '11 later XL 883L) *** some conflicting info
'00 - '05 Dyna models
'00 -'02 Softtail (except FXSTD)
'00-'08 Touring

 

Good job, this is correct. Now back to bearings. Over the years you listed, there was three different size wheel bearings used with three different sized axles. 3/4", 1" and 25mm. Generally 3/4" was used through 2005, 1" for 2006 & 07, 25mm 2008 and newer. Any of these wheels can have any size bearing fitted.

 

My 05 has a 1", the wifes sporty is an 07 with a 3/4.