Get a couple PT 2x4x8 and place in gutter to lesson the gap/transition between street and d-way. We have same set up, but discovered we don't need the 2x's afterall. Take your time and have a spotter or 2 outside watching all angles and possible points of contact on truck, d-way and trailer on both. The leveling jacks or legs (if so equipped w/ 6 pt level up) could hit 1st while backing up. Once in d-way, not sure how much of an angle you have, but it may NOT be possible to level 100% for back end "may" hit. If not, cut up a 6x6x8 into 18"-24" lengths to place under front legs to shorten the gap between pad/leg and ground. Also, may have to tinker here, but add a wedge or so, so pads are level when the hit the blocks of wood. As for remaining pads/legs, we cut up 2x10 (or 12) into 16" lengths and screwed 2 together and attached a handle to 1 and place them under each leg for support on grass as well to cut the gap down. As for chocking your wheels in d-way, well you could at 1st, but if you level it, may be a chance you'll lift tires off the ground so chocking them won't do you any good----again depending on pitch of d-way.