Well first go out and rent one and see what you think! That's the best way
Opinions are like a$$holes everyones got one?
Myself and the BSR ride 2 up 75% of the time started on a new Heritage and loved it as we rode more and more miles we added detach tour pack.
Upgraded to another Heritage did a full blown custom with full detach tour pack and bags Loved it too.
Did fly and rides all over and rented Road Glides Classic's and Street Glides before deciding.
Rode Vegas, Flordia, the Blue Ridge, North & South Dakota and Wyoming on Rentals
Finally bought the CVO Street Glide and added the matching detach tour pak. If she is on the tour pak is on if she isn't it isn't. Works perfect for us and there is no difference in the ride from an Ultra except I thin the new Hydraulic shocks work better than the air do. You can order them.
The 18" wheels are a looks thing but if I were in your shoes I would stick to the 09 or newer as the frame difference is really a big plus!
I ride them all at work for an independent shop and not knocking a deal on older but all things being the same I would not buy an 08 or older. Of course funding always affects this call?
Only you can decide but if your drawn to the Street Glide buy it and make it your own!