..first time encountering this.

Not using a mod such as Go To Jail, it seems easy to get into a non-resolvable bind.

I got detected taking equipment out of some Redoran's closet (an NPC managed to open a door and walk in!) - got tagged with a bounty of 22 thousand gold! Meanwhile, I had just been expelled from the Thieve's Guild. I didn't think it was permanent, but whatever the case, I am deemed to have no honor and can't make amends to rejoin and remove the price on my head. Jim Stacey's gone; I'm theoretically the head honcho.

Guards all the while will not engage in dialogue to allow me to pay the fine. They just say 'Goodbye' and attack on sight.

So it seems there's no legitimate way to clear a high bounty. Of course no other NPC will engage with you (at least without major magical intervention), so playing the rest of the game as a full-on outcast seems pointless.

Am I just missing something or is this a design shortcoming? (If there is a way out, remember to use a spoiler). Thanks.

I have no idea whats going on, never encountered that problem. As for the goodbye dialogue thing, theres a way to get around it, but I don't know if it'll work in your situation. Take off all your clothes and talk to the guard. Yes, really. It forces the "hey, you're naked" dialogue to show up rather than the normal default.

Another way would be using Calm magic on them til you can talk to them. Aside from that... I don't know what you could do, short of using the console to massively cheat. Which is totally an option.

"SetPCCrimeLevel 0" without quotes if you cant find another solution.

The naked thing is a hoot, but unfortunately no go. I guess they want to skin me.

Calm Humanoid stops the guard's immediate attack, but the moment you try to talk to them you just get 'Goodbye' again.

To continue playthrough, I've gone the console route, but of course it's not really 'legitimate'.