First, you should read the one star reviews on that device. Trust 1-star reviews on Amazon, especially if you are less technical.
Even one of the 5-star reviews says the device is functional at 30 feet only part of the time, and with lots of interference. And in the reviews that say the picture is black and white, it's because they aren't getting enough signal for color.
It doesn't actually look like the transmitter is waterproof. It looks like it's meant to install within the vehicle, not on a trailer.
If you go through with this, you need to make it so that there is an unobstructed line of sight between the transmitter and the receiver. The aluminum skin of the Trailmanor is likely to block the signal, so you really should get the transmitter on the roof.
Your ideas for powering it would work.
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