However, it sounds like it may not be the best idea with the complications if I ever were to try to sell one unit.

. :)And my situation is even more complicated since I'm on the other side of the country quite literally, so it will be pretty hard for me to drop by every other day :)Another question I have is how many details an estimate should have.

I am afraid that it would be complicated to deal with the owner of the other half since it is duplex.

I was originally exploring S-Corps and C-Corps, but I think for just starting off with some small projects, it doesn't yet make sense to pursue a complicated structure.

Due to our claims-free history, we are in the process of switching our home, auto and umbrella to a carrier that appears to have the best claims record, which is key to us given the fire history in California where a few of our neighbors have had to go into the high risk pool.The complicating factor I face: we want to keep our options open to offer our home as a PART-TIME short term or corporate rental (so the average rental stay would be 30 to 60 days).

Due to our claims-free history, we are in the process of switching our home, auto and umbrella to a carrier that appears to have the best claims record, which is key to us given the fire history in California where a few of our neighbors have had to go into the high risk pool.The complicating factor I face: we want to keep our options open to offer our home as a PART-TIME short term or corporate rental (so the average rental stay would be 30 to 60 days).

When I did airbnb for a few months on my Pensacola SFH, I remember the taxes being a bit more complicated than a regular long-term rental.

The first lawn quote I got was $40-50/visit while the snow quote is a lot more complicated as it breaks down plowing, shoveling and salting as well as has tiered pricing based on snowfall. 

Seems like a very complicated system to bring to market.

It gets a little complicated but once you think it through it's easier to follow.