Another bonus of the pigtail for a Tender is it's the same pigtail you can use for heated gear. That was essential for long distance commuting (180 miles) during the winter 15 years ago or so. I haven't used it much since, but when you need it, it makes a huge difference.
True, but ya probably shouldn't. I think my Tender lead has a 3A fuse in it, and the heated gear lead has a 15A fuse in it. Circuit protection exists to protect the wire, not the device, and although the odds are slim of anything going wrong with your bike on the Tender (with a 15A fuse so you can use it for your heated gear), eh, it's not a risk I like. Two leads is a little fiddly and doesn't look as nice, but most of the new heated gear takes a different connector anyway.
As for shoes... uh yeah. I've always been an ATGATT guy, except for ONE day when I was getting ready for a trip and decided to ride my XT225 the 1.2 miles to the gas station in jeans, t-shirt, helmet, gloves, and running shoes. IT'LL BE FINE! Hahahaha. The gods were laughing at me. I got to the pump, tried to put my left foot down, and the lace was caught over the shift lever. Did the herkyjerky weight transfer maneuver, and found that my right lace was caught on the brake lever. Fell over that way. Clunk. Dirt bike. Only damage was to ego.