Hello fellow HW256 owner.
I needed to replace my HW256 also (gonna miss the slideout front storage and cassette toilet). I considered the Roo 23IKSS but ultimately felt uncomfortable towing something that big. I just do not have the TV for something that big. I like to stay sub 5,000lbs of towing capacity as it gives me a wider choice for TV's. My storage situation is also not the best as I park my unit in my driveway and a HW is tall enough. lol.
My wife was not a fan of the bed situation. The hybrids do not seem to have a fully smooth sleeping surface. The one sleeping on the camper end of the bunk needs to straddle some uneven joints. You can search for hybrid bed solutions. Many people complain.
Floorplans are awesome in hybrids and the extra storage is fantastic. As you pointed out, no more roof raising.
I have settled on a new Rockwood HW296.
Good luck with your decision.