New long tail owner here. Do you guys mount your motors with the tail in the boat while towing or leave it extended? I always thought you reversed it and put the tail in the boat but the guy I bought it from drove with his facing out

If you can swing yoir shaft around into the boat, that is the preferred method. Transporting any boat, over land on a trailer, causes the motor to put stresses on a transom that it was not designed for. Be it a longtail, surface drive, or outboard, are made to sit on a transom and push. Like a bulldozer. When towing, the motor jumps around in all directions. None of which are the ones it is designed to move in. If the tail has to hang out, make a transom saver, and try to stabilize It as best you can. On my rig I remove the shaft, remove the motor from the mount, and place them on the deck of my boat. I have a Mudskipper setup with the 420cc predator engine with loop header and cavitation plate.

If it doesn't swing into boat, then get a good ratchet strap, center motor with handle is boat. Wrap once around handle and then wrap around boat and trailer and then ratchet down tightly. the motor will "bounce" some. I towed a 16 hp GDLT like that for better than 10 years! With no Problems except sometimes I would lose my flag so I got a roll orange marker tape!