We just sold our 19' travel trailer and purchased a 30' 5th wheel. We've only taken it on a few weekend trips, but here's what we enjoy so far:
- 5th wheel is easily hitched and unhitched without assistance
- drive is very stable. A little bounce over big bumps, but zero sway
- lots of storage. You're correct, you'll still need to unload your truck for security, and you can put more than you think in the bed w/ a 5th wheel, especially a long bed.
- Sway bars and stabilizers are a thing of the past.
- 5th wheel seems to do better in strong winds.
- You could consider a toy hauler for your kayak.
- One other possible advantage of a 5th wheel is that you can park some gear under its neck when it's in place