Thinking about this some more...
Yeah, the gear can be a hassle -- one that I think is worth the trouble, but a hassle nonetheless.
On the front end, putting on the suit is (almost literally) a snap. The Roadcrafter goes on very quickly. Worse are the boots -- wrestling the pant leg over them is almost enough to make me take the cage. Whining, for sure. Dress pants with a straight leg do fine, but the Wrangler 13MWZ's, with their cowboy boot tapered leg, need silicone -- or something -- to get them over the boot. And I have skinny calves. May need to start buying Carhartt or other jeans with a wider, boot-cut leg.
Sometimes I'll wimp out and take the cage because I don't want to deal with the suit at the destination. But if I challenge myself a bit and just go, I find that most often some accommodation can be made. I've gone to business lunches at nice restaurants, and the host/ess will find a place to stash the suit while I eat. Hospital nurses offer to keep the suit at the nursing station (probably so the dirty suit doesn't go into the patient's room). Other offices (doctor, professional, etc.) usually have a nice receptionist that will find a temporary home for it. Eight times out of ten I don't even have to ask. For the other two, a polite request is usually met with a favorable response.
The only challenge is running errands and shopping. I now just take the suit off and stash it in the cart for the duration. This has had the unintended consequence -- and benefit -- of changing my shopping choices. Rather than take the suit off at Home Depot, I just wear it into the local Ace Hardware -- where several employees are always ready to help me find what I need right away, get it, and get out the door in a hurry. Same thing for the quick food runs.
The last hurdle is government offices. Standing in line at the post office with the suit on is a bit of a drag, so I take it off, park in a corner somewhere where I can keep an eye on it, and go about my business. No complaints so far. Same thing at the public library. Other government offices are less accomodating, so I just wear it. The good news is that I don't have to visit them very often.
It's possible to have some fun with this. Two Saturday's a month, more or less, the local Harley dealer has free food for lunch -- hot dogs, burgers, etc. If I'm in the neighborhood and hungry, I'll stop by -- in my flaming hi-viz yellow Roadcrafter on my KLR. The looks and reaction I get from their normal clientele are truly priceless.
The only problem I haven't been able to solve is how to deal with the suit if I want to park the bike at, for example, a trailhead where I want to hike. Given what I spent on the suit -- it's a semi-custom job -- I'd like to secure it and cover it somehow. Still working on that one.
I think the hassle factor, if there really is one, is largely in my head.