I can't help with the cubs. Maybe Dan can (he's more on top of those types of thing).
Popups can be a lot of work, mostly dealing with packing, organizing and the setup and take-down.
Hybrids have some of the same work involved but the organizing is much easier in my opinion. You still have some setup and take-down with the bunks, although that only adds another 5 minutes per bunk when I have help from my kids and a little more when its just me.
The sailboat has less wind resistance and typically a lower center of gravity than a hybrid or any other non-popup trailer. Towing a travel trailer is kind of like pulling a sail behind you. Still there are few to no hybrids with a GVWR of 7,000lbs so you're good to tow any of them with your truck.
DW, 3 Kids and our Goldens
2012 Shamrock 233S
2008 Toyota Sequoia 5.7L 4WD