Mike, I'm no spring chicken either and have come up with some helpful things.
1. Wheeled dollies. Have some HF cheapos, but the casters are pretty shitty and that's exacerbated when loaded heavity. Better luck with some mo' betta castors on chunks of plywood.
2. I really lucked out and got my adjustable height table for $20, but it only goes down to about 28 or 30" or so. I haunt Craigslist and have looked at the old air over hydraulic bumper style jacks that go for cheap sometimes. Won't work on most newer cars 'cuz they don't have bumpers per se. Remodeled some it could be a inexpensive platform lift. Here's a pic of one just so you know what I'm talking about but I've seen them for much less.
https://boise.craigslist.org/tls/5937797504.html3. Interesting idea on the sheetrock jack. I've got one, but really can't see how it would improve things without some reconfiguring and as much as I don't like drywall work, I may still use it someday.
4. Board foam. It's got some cushion, but not so much as to be mushy. On floor, on bench, wherever. I see it as sacrificial, and I generate scraps through various projects.
5. I've been know to build jigs that I'll cut up or throw away. Sliders, ramps off bench
6. Levers, pipes, wedges.If men can move rocks like Stonehenge into place with similar, one can probably figure a way to move a speaker
7. Furniture pads. Again something I already have, but have used them to slide things without damage.
8. Although I've never used one on speaker building, I have moved full refrigerators with this which is almost fun:
http://airsled.com/9. Another thing I've done is to use lighter material...sometimes as a sandwich. One of the reasons I'm not MDF's biggest fan is it's just so damn heavy.
I think about it some more, perhaps come up with more