We got into hosting because we (well I) fell in love with our old schoolhouse and needed to figure out a way to have it make financial sense. My husband wanted to rent it full time as a landlord. Where is the fun in that?? This way we can enjoy it periodically ourselves.
We currently own 3 houses. The main one is a carpenter gothic (vernacular style) 1908 farmhouse with a big wrap around porch and 2 additional side porches, kitchen stairs and an attic with a window seat in the gable. Its basically the house I wanted as a kid reading books like "Anne of Green Gables." There is an old dairy barn in the back which I would love to convert to a guest house/painting studio.
The Airbnb is a converted one room schoolhouse built of solid stone in 1850 or a bit before. It served the families who worked on the Francis Scott Key estate. Its hand built and there isn't a window of standard size (or really the same size) in the whole place.
We recently bought a condo for friends and family to enjoy in an old mansion in New Orleans, also built in 1850. It has 13' ceilings, wide plank heart pine floors, and a huge balcony with walk out windows, fireplaces (nonworking) in every room-- 2 have original tile and all have original mantles. That house was built by a prosperous free person of color (the Treme' neighborhood where it is located was the only place free people of color could own property.) There is a legend about a stolen necklace attached to this house and the homes on either side. (It seems to have survived Ida okay, thanks to those of you who asked!)
I don't know if this "hobby" has a name, but I am crazy about old houses. On the weekends we sometimes just go and tour places. I stalk real estate listings like its my job. I do fear it could bankrupt me one day! I feel strongly about preserving original features when it makes sense, and don't know if I could live in a place that was new construction. Am I alone?