Okay I know what to do from here.

First, reverse pickpocket poison apples into all of the guards inventories, then hang out in their barracks until they all eat poisoned apples, once the guards all die steal their stuff and sell it to the town merchants. Now not only are you richer, but the town's guards can't arrest you on account of being dead.

The best part is that when the guards eventually respawn they keep the poisoned status and will quickly die again, with a new loadout of guard equipment!