How long is it to the dead end from your driveway? You will need enough length to get the back of the trailer past the end of your driveway. Other than that I'm not really sure what the problem is. I have a setup very similar to yours. The neighbors driveway is offset past mine a few feet and their mailbox is where your fire hydrant is and that has never been an issue with the front of the truck. When we first moved here I tried, once, to use the neighbors driveway. That was the first and last time. It made it ridiculously complicated. I now pull past my driveway (toward your dead end), and back in, at a 90* angle. I also have a ~10' gate at the back of my driveway I have to get through to get into the back yard. Usually I'll end up having to pull forward once to get the angle just right to make it through the gate as well as making sure I can see down both sides with my mirrors. I block the entire street and the truck almost ends up in my neighbors front yard, but stays in the street, but whatever. People can wait for a minute or two (I'm at the very front of the neighborhood). Entire length is roughly 55', never measured exactly (37 + 20 - 3 give or take).
I also have to run over the "curb" exiting because the nose of my truck just misses the other neighbors mailbox. What is the problem running over the curb? We have those "rounded over curbs" here, not really a "curb", but if you have a real curb and it bothers you with your tires or whatever, put a board or two down to make it less of a "hump/bump".
My biggest issue with my setup is the stress it puts on the tires and suspension, but there's nothing I can really do about that but move.
2014 Raptor RP300MP w/ Rear Patio Party Deck, Folding Side Ladder, 6 Point Level Up, Carlisle Radial Trail HDs
2004 2500HD D/A CC SB - TTT Mirrors, Prodigy BC, 18K Pullrite Superglide, NEW Fuel Injectors 11/2015 (ouch)