Riding a 2011 RGU and when I hit a bump in the road it feels like I have no shocks at all. On one dip in the highway, the shocks bottomed out so bad, the frame hit the ground. Shocks are pumped up to 50 pounds and I don't see any fluid leaking. What else could be wrong? What can I check?

 

First thing quite a few people do, is change shocks.
Those factory air shocks are about the worst thing out there for "comfort".

I chose the HD Premium Hand Adjustable (13" Version) for my Street Glide.
I ride 2-up 99% of the time, and these shocks are a huge improvement.
Wife and I are both very happy with the ride now.

There are also other options, such as Ohlin's. Those are probably going to be even more comfortable, but at a higher price.

Lots of options out there if you do some research.
Just about anything will be better than the factory air shocks.
Shock threads are right up there in popularity with oil threads.