Air ride! 5 1/2 inches from fully up to dropped down. Can be done for less than $200. Rides better than stock.

 

New pair of thick sole HD boots, worth the money. Lower rear shocks, HD, $400. Chrome Werks 2+2 bars, puts you back in the seat, and slightly wider. Feels like power steering! Haven't touched the front yet, thats my next step. These steps, have made this much more comfortable. Feet on the ground. No sacarfice in the 2 up ride, loaded. 2008 FLHTCU. You can do the rear shocks, and think about the front, later. 1,000 of miles, on this set up. I'm looking at the Progressive cartridge drop in's. Much easier self install, but another $400.

 

I put Street Glide shocks on mine and I have never had an issue with the ride when two up.