"Can you pull a boat behind a 22 foot hilow?"
Maybe, just remember, CAN is not the same thing as SHOULD.
As far as CAN goes, you can use this website...
AAA/CAA Digest of Motor Laws
...to check the jurisdictions you're interested in.
I've looked into this for my rig. Oklahoma has no specific restriction on the number of trailers, as long as the entire combination doesn't exceed 65' in length. My pickup, camper, and pontoon boat combination (19' + 22' + 30' = 71') is too long.
SHOULD will depend on driving ability, equipment, weather, traffic, distance, political affiliation, and the skill of your guardian angels.