That happened in my campaign. Well, the bandit leader turned warlord got a knighthood. A PC party did the go-between negotiations. It’s how I ran the Harn adventure “Trobridge Inn”.The more popular route, I believe, was to find a lawless area and loot and plunder it until the local authorities decided that the easiest solution was to grant you the legitimacy of a title, and then tax you.
Off topic a bit, I love the medievalism of Harn - a non-D&D medieval fantasy RPG.
For off topic, my wife and I just discovered “Last Kingdom” this weekend - solidly medieval feel built adjacent to real history. It’s a TV series from 2015 to the present about the period c. 869 AD in England - we just saw the episode where the Vikings killed King Edmund (later St. Edmund) and ended the Kingdom of East Anglia.
Anyhow, if all these title and marriage questions are not rhetorical, the history of the period you’re recreating, or the fantasy you’re recreating, will tell if cash for titles is a thing or not.
Some other good sources for medieval feel:
- Brother Cadfael novels or TV series (zero fantasy, historical fiction)
- The old movie “The Lion in Winter“ (zero fantasy, historical fiction)
- Game of Thrones novels and TV series (medium fantasy, sometimes “history informed”)