MortalPlague
Adventurer
Clearly pimped out wagons and butlers will have a lot to do with it.
As an aside, my current campaign has something like this going on. My PCs are 19th level and pretty mercenary. We wrapped up the previous arc with 2 PCs inheriting 12 manor houses throughout the countryside and the title of Count / Countess in the city. So they spent a year of down time touring their houses, and accumulating a bandwagon of strange and wonderful followers. Their retinue consists of:
Catherine - Deva Butcher
Noddil - Deva Baker
Sephestro - Deva Candlestick Maker
Quira - Eladrin Tailor (and her assistants)
Antonio - Purveyor of Alcohol (modelled on the Most Interesting Man In The World)
Moller - Fire Genasi Apothecary
Xialla - Shadar'Kai Dancer
Lixle - Half-Elf Tiger Tamer
Montgomery - Human Treasurer (who they allow nowhere near their precious treasure)
Pear - Tiefling Chronicler
Portmouth - Dragonborn Lawyer
Eclaire - Lightning Genasi Painter
Jannoxel - Drow Ex-Slave (rescued in a previous adventure)
Fizzban Whistlesnout - Gnomish Alchemist
Tallera - The Boy (who is, in fact, a 12 year old girl)
A Troupe of Halfing Acrobats