You live in Rhode Island...Got an old hockey puck or similar laying around that you could JB Weld onto the foot of that sidestand? It, or something similar, would present a broader surface to the ground, and should also raise the angle of the bike to near perpendicular, which might help with the cold starting.
Given the health circumstances, you might also get a pass on using that "electric leg" from here on in. I hardly ever used mine, but I am also quite sure that the previous owner of my Iron Belly hardly ever, if ever, kickstarted the thing throughout its initial roughly 4,500 miles. Its sprag gave out at about 7,000, if I recall correctly. So, I'd say if you're running the standard 420 ml (in an AVL?) of fluid in your primary, up to the fill level hole, go ahead and dump in another 400 ml or so to better bathe that sprag, and if it comes down to enjoying a nice ride or not, go ahead and fire her up with the button.