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Go for the side-hack. You've already got a great motorcycle, just add the hack and keep riding what you know you really want. Weight shouldn't even be a concern then.
Ankle and knee brace and practice your stops 1 and 2 up. I wear a ankle brace all the time, works great for me. They all weigh the same when they get rolling.
Like you, I am also a large person. I went from a Super Glide to a 09 EG. I have had 2 complete shoulder replacements, and a total left knee replacement. On the third day that I had the bike, two up, I dropped the bike. Really pissed me off, but I had to learn how to ride the bike a different way when stopping. I slow the bike down with the back brake, them with my legs already down, I stop the bike with the front brake. It works well for me, either one or two up. My problems are solved as for as I'm concerned. I understand your ankle problem, and sympathize with you, but I was not going to let it beat me because I love my EG. Good luck with any decission you make.
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