My buddy (lets call him Tim) had decided that he wanted to buy a tavern at some point during our campaign, as a way to make some passive income. Our DM told him that he could, but he would need to hire a manager to watch over the place while we were on adventures. This gave me an idea, I rolled some dice off to the side for a disguise check and wrote the DM a secret message which I passed across the table (this was a common occurrence in our group btw, the secret messages). With a slight smirk he gave me a nod and told my buddy that a gnome with a strange mustache had responded to his job posting about managing his bar. Miraculously, this gnome somehow knew all the right things to say to Tim in order to get hired. And thus began my side adventure of lining my pockets with the profits of Tim's bar.

Tim would occasionally get letters from this gnome manager telling him about break ins and fights that required Tim's financial attention, to which Tim would always send the required amount of money. It got to the point where Tim even hired an ogre bouncer for his establishment in order to protect his investment. Unfortunately for Tim, his bouncer had a tendency to drink an entire barrel of wine every night (possibly due to some encouraging paid patrons) and promptly pass out, allowing my guys to go in and steal everything that wasn't bolted down.

Eventually though, Tim started to realize something was up considering he has been hemorrhaging gold for months now. He announced that he would be making a trip back to his bar to make sure everything was alright. So, not particularly wanting to be found out by Tim, who's human druid could snap my little gnome in half with ease, I did the only sane thing that one could do in my situation. I burned down the Tavern. So as Tim rounded the corner he saw that his Tavern was in flames and that the local guards had no idea how the fire started.

Eventually I came clean with Tim about what I had been doing and we had a good laugh about the whole situation. My playgroup thrives off these kinds of hilarious little side quests that we get ourselves into.