Billy, count me in as one of the "we're-still-boating" crowd. I was one of those upper Mississippi River rats that had a boat before I could drive a car, and have always had a boat (of some kind) ever since. Nice rig you got there. ...and dry docks are sooooo much easier than waiting for people who can't back up their trailer at the boat ramp! One word of advice, use Stabil in the gas tank if the gas won't get used up within 30 days. Gas does very bad things to motors when it sits too long, especially if it contains ethanol.
Here's a newsflash on the subject of boating: I bet I'm the only one on here who tows a boat behind our TM! It's a 16' jon boat with 25HP. At less than 500# (boat/motor/trailer), we haven't noticed any undo stress on the TM or TV. As an added bonus, we get better mileage in double-tow mode because we slow way down for safety (read sway) reasons. Had to rig up my own trailer wiring plug. Made a 7-prong input into TV that splits 7-prong for TM and a 4-flat for boat trailer. (Only used 6 prongs on TM because backup lights obviously become useless in DT mode.) Works well and entire 3-rig setup meets the double-tow laws where we run out here in CO/NE/KS. Someday we'll get a 14' car-topper V-bottom to eliminate double-towing, but for now this gets us out on the water...
Quick thoughts for the "Hey DW, he did it! I can do it too!" gang. 1. We can unhitch the boat and push it around ourselves if we get into a jam. Haven't had to (yet), but something to keep in mind. 2. Gas stations can get "interesting". I've had to use a 5 gal gas can to fill up the TV because I couldn't get near the pumps (at least not without getting myself in a jam). 3. Dealer said TM can take it, but who really knows? A 500# rig behind the TM is the max in my mind. Have to consider tongue weight and other stresses on TM. 4. DT laws vary by state (some states call it triple tow). Some don't allow double-towing. Others only allow DT behind a 5th wheel. 5. Double-tow gets the job done, but using a second car with its own hitch would be preferable. We just don't have that option at the moment...