And wouldn't Using a self-assembly dolly be much more awkward?

Yes, it would. A fellow club member of mine has an ASW-15 which came with the old style trailer (fuse nose first, wings tip first and to make things even better the glider had to be loaded and unloaded over the trailer hitch) and he bought an Udo rigger after seeing how well it worked on my 15B. He manged to use the one man rigger successfully but it required a bit of to and fro movement. His old trailer did have a dolly into which you put the wing root leading edge as you removed it from the trailer and allowed you to roll it instead of carrying the weight but all in all it was still a lot more awkward than it would have been with a root first layout. Eventually he replaced it with an Avionic like I have and is much happier as a result.

If I recall correctly Eric, I think you've seen what I consider the worst glider trailer ever made when you came to Valemount during a Vancouver Soaring Association trip to that field. We had our Twin Astir there in it's Swiss made trailer. In that one the fuse went in tail first, the wings root first, the left wing on the right, the right wing on the left. The fuselage "dolly" was a framework that picked up on the wing fittings and engaged steel tracks in the trailer. Because of this the moment the nose came out of the trailer the glider was riding on its main wheel necessitating the removal of the canopies in order to give a good place to hold on for the two people who needed to keep the fuselage upright until both wings were on. You can imagine how much fun it is trying to keep the fuselage steady when putting the second wing in and attempting to make all the fittings line up! When taking the wings out you had to walk the tip out holding it about three inches from the ground. A little higher and the trailing edge would scrape the trailer, a little lower and the leading edge would scrape the trailer. The trailer was an oval aluminium tube just barely big enough to fit the glider and had no door at the hitch end. About 50% of the time when putting the fuselage back in it the fuselage tail fitting (also riding in a steel track) would bind on a rib requiring pulling it all the way back out and trying again. Naturally the tailplane rode in a saddle attached to the rear fuselage making the tail heavier to deal with when extricating the fuselage from the trailer - because of the layout it was necessary to undo a strap connecting the tailboom to the captive tailwheel fitting in the trailer, lift, tilt, move forwards carefully until the tail end was clear of the trailer.

As far as I can tell the idea behind putting the roots and fuselage nose at opposite ends was to allow the placement of the axle along the trailer in a position which improved stability on the road. The funny thing about that is that all the Cobras, Komets, Avionics, Mindens,Schreders etc. I've towed have been very stable whereas quite few of the trailers laid out with roots and nose at opposite ends have been nightmares. The Twin Grob trailer mentioned above started swaying badly at anything above 70KMH on the way back from Valemount. Long, long drive back to Hope that day...