I drive a DRW every day, including through a narrow access-controlled gate with height restriction bar over it. My antennas hit the bar, but I have no issues driving it through the gate.
Length and width can be a concern when parking. Find a pull-through out from the building and walk a little or back in along an edge. Exercise is a good thing. My wife is 8 months pregnant and we still do that, although I do try to find a pull-through a little closer in now. She likes to walk.
Drive-through? Park and walk in.
Worried about fitting in somewhere? Google Earth is your friend. I've used it to find suitable parking well in advance if there was any question.
As for registration, that's usually based on GVWR or what you want to pay relating to weight. Just make sure you register it for the most you ever carry.
Insurance? The only thing I ever found was that my insurance company sent me a question sheet about 6 months in asking how many miles I drove for work, etc. They wanted to see if I was using it for business.
I love driving it, and the few hassles are nothing compared to the safety, stability, and suitability of the truck.