How bad / unsafe does the level of this trailer look?

It doesn't look safe but if guys are using them than I shut my trap.lol I'd much rather one chunk non adjustable drop hitch

 

I usually tow with a bit of a rake like you have there, not as much, but maybe 6" to level. It's a 5x10' utility with a drop gate. Tows great, and I've locked them sumbitchin tires up on my truckboattruck a few times, jumped a few ditches and towed damn near the world with it, always pulled true.

Honestly, I prefer a level ride always, and keep it at 65MPH when towing as most trailer tires aren't rated higher than that, but I think if you take it easy you should be good.

However, giving the trailer a rear tilt is gonna introduce more sway possibility in your equation. I'd front load the trailer a bit more, or at least in front of the trailer axles as best you can to try to keep some weight off the rear.