Much of the attraction with that sort of thing as far as the band is concerned, of course, lies in the fact that you can take the travel side of things right out of the question. Book a theatre for a fortnight, promote the shows yourself, cut out the travel expenses, set up the gear once and (presumably) leave it there. Ideal. Keep costs down and maximize profits.
The fans know to expect it, and you can probably be certain of selling out a suitably sized venue. So it's all cream once those initial expenses have been met.
Touring, of course, is probably going to be the bread and butter side of your operation, so you're going to end up working something close to a circuit, preferably one that encompasses areas where you do well, and while the fans who live elsewhere (with northern Australia being a prime example) mightn't be too happy, the economics of getting to those markets probably rule them out.
If they don't actually rule them out, they'll have an influence on your format when you get there, which means that I'm more likely to see Elvis Costello or Richard Thompson in solo acoustic mode rather than in a band setting.
In those two cases you're talking performers who write rather well, are prolific enough to turn out a new album every so often, and have a large enough back catalogue to be able to sprinkle familiar material through the new stuff so that the audience isn't going to be grumbling about all this new stuff. Those extensive back catalogues mean there's enough material that can be tweaked to fit into two (solo acoustic and band) or maybe even three or more (Costello solo, with the Imposters or the Sugarcanes and in a big band or orchestra) settings.
Neil Young's another one who can fit that back catalogue into whatever format he's currently playing around with.
At the same time you have the rather prolific Stephen Cummings who manages to release a steady flow, mixing new material and reworking that back catalogue. He doesn't work live all that much, but presumably pulls in enough from what he does, combining what he gets from royalties, the odd gig here and there and the occasional excursion into fiction or other journalism-related formats, to get by.