Welcome to the club.
I would guess a demo unit would be a great way to go since any factory "bugs" are probably already taken care of by the dealer without any real wear or tear.
Regarding your Tundra, I'd be willing to bet that Toyota has available the 7-pin connector wiring harness that would be a simple swap from your existing 4-pin connecter. You could do it cheaper but the plug-n-play from Toyota would be easiest.
I agree on the Prodigy controller just make sure you mount it so you can easily manually activate the brakes if needed and for the pre-drive test.
As far as the WDH, my experience has been that a 1/2 ton pick-up will very easily tow your TM without. I went a couple of thousand miles without one before I elected to get one as a safety precaution (after reading the various posts here). All in all I consider the WDH as pretty cheap insurance. When a group of deer suddenly popped up in front of me around midnight last fall and I was able to swerve hard and miss all but one, I was very grateful for the added control. RockyMtnRay has some great posts on the subject. Bottom-line a WDH is really for when something suddenly goes wrong -- road debris, blown tire, & other evasive maneuvers where the extra steering grip is really needed.
Finally, I get about 15mph with my F150.
Again, welcome aboard.
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