For the lugs, just get a 4 head X wrench. Will cover anything you have.
Our 1007 had the same problem. I used to carry around a car jack stand. Lift the tongue, drop frame down on the jack stand, lift the tongue jack up and pull the wheel, tongue jack back down to the ground (wood block under) to lift the frame off the jack stand, then drop tongue onto the hitch.
That got really old really fast, so I bought a lower profile foot instead. We never really liked the wheel anyway as it tended to sink into soft ground. Can't figure out how Jayco could get the geometry so wrong. And yes, the hitch was at the correct height to tow the pup level; no WD required for such a lightweight trailer - the OP's 8' Sport is considerably lighter than the 10' 1007.
2011 Jayco X19H (purchased 2015)
2008 Jayco 1007 PUP (purchased new, traded for the X19)
2012 Chev Traverse LT with TP