Getting TT up a steep driveway?

If you're moving the trailer in and out a bunch of times a year, a permanent solution along the lines of what I wrote above is what you need to do.
The other solution, that I'd be inclined to do if you can line the trailer up dead straight perpendicular to the sidewalk/fence, and don't have to "turn" the trailer as you're backing in (which prolly means you're pulling onto the neighbors front lawn across the street)
is build a couple ramps you can drag out there and bridge over the dip.
Short of that working or the construction project, limit yourself to an off road camper, single axle, may give you the rear departure angle needed, or flip the axles on a normal camper, big a tires as you can get on it and lower the hitch to the ground almost when getting it in and out of the yard. And hope the sewer pipe or something else don't hang down in the back.

I agree, the best way is to flatten that sucker out, however I see more than just a little "re-grading" and slap some pavers down. Your whole yard, fence, house, the city sidewalk is built around that grade separation from the street to yard level and I'm assuming the yard is relatively flat at the upper elevation behind the fence.
(Been moving dirt from jobs like this to half million yard roadway cuts into the side of a mountain for a while now, lol)
What I see is, you cant change/raise the sidewalk, but you'll need to flatten that ramp out a considerable length, into the back yard, behind the fence.
If the gate is wide enough to accept the trailer width plus a little gravity block retaining wall on each side, you could cut a "slot" through there and stack a landscaping block wall along each side. Or could take out the far post, and widen the opening to do the same.
Then gravel, paver, etc the new lowered driveway. Note this will require even more width if you relocate the gate to within the 2 walls so it can run down to the new ground level.
This isn't a day for a contractor or a 24 beer diy job.
All in, you're removing gate and part of the fence,
excavating the slot, grade/prep/install about 150-200sf? of retaining wall, re surface the new ramp, new posts and gate.

dhatcher wrote:
Yeh wife and I have quickly been coming to the conclusion, re-grading seems the only way. In order to do that though we'd have to chop up some of the concrete pad at the top. May have to look into off site storage. :/

IMO, it's a no-brainer to have it regraded - regardless of the work involved. At least have a contractor come out and take a look to give you options. Storage at home is way better than off site. Upgrading your approach will pay for itself in the storage fee savings.

Yeh wife and I have quickly been coming to the conclusion, re-grading seems the only way. In order to do that though we'd have to chop up some of the concrete pad at the top. May have to look into off site storage. :/

Is it possible to regrade that drive? Be a one day job for a professional or a weekend job for you with rented equipment.
I don't see anyway around it.

In your picture, that sudden change from a level surface to a steep incline is much more severe than my driveway that I described above. There is no trailer with enough ground clearance to clear that incline. You would need to use a large ramp which would be a pain to deal with. I would always prefer to have my trailer at home, but a storage facility might be best in your situation.

Camping is suppose to be fun adventure, from the moment you leave the house until you return. Our current driveway reduces the fun of camping so we decided to move to a more RV-friendly property.

Well it is there in front of a RV Gate (or did you put that in), how did the previous owners do it?

Your only choice would be some very long steel or aluminum ramps. But I would guess they would have to be nearly 20 to 25 feet long to work (and even then may not work). Something that size is going to be expensive, is going to be heavy, and is going to be a bear to deal with. If it was me, I'd look for offsite storage.

I'd be inclined to get two sheets of 3/4" plywood and place them side by side (lengthwise) so each would take one set of wheels. Then place fixed wood blocking under each one so that they won't move when backing over them. They will be heavy to move but with enough blocking (to prevent buckling) they should work.

Flattening the crown so it is straight would help. Those bricks look like they are cemented so it would be a bit of work. Also, could you lower it a bit for a few feet inside the fence gate? A couple of planks on the sidewalk while backing might raise it up enough too.