I tried the backwards trailer setup.
Looks like having the boat hanging that far off the back of the trailer would severely reduce your tongue weight, may even induce negative tongue weight which is likely to cause trailer handling problems like fish tailing.
I also would not want that much boat hanging behind the trailer lights. I believe in our state, anything hanging more than 3 feet behind your lights requires a flag.
Overall, I don't see much advantage to trailering backwards and probably a lot of reasons not to do it.