Not calculating your basis properly between building and land, which impacts depreciation. 2.

I also have a building though in a low income suburb and that place is 10x the work and I kind of want to find a manager for it.

It has taken me time and I am ok with building long term wealth vs spendable dollars today.

With the network I have been building I am confident that this will be a viable option in 18 months.

Thanks for the vote of confidence @Tyler Carter! 

I would look for a 2 bedroom 2 bath duplex with a one car garage for each side located between the two units and each front porch on the each end of the building.  

An example might be a commercial tenant with 50% of the space in a building sends an after-letter notice that it now plans to vacate at the end of its lease term in 6 months.

Glad you are setting aside money, but if the HVAC is 20 years old, or the septic system has never been pumped, or the roof is 25 years old, etc; you will get hit with a cost before your build up enough set aside.How stable is the other tenant? 

They won't be able to fix that problem as there is probably a small leak in a pipe or a crack in the foundation or a bit of water coming in from somewhere or moisture building up in the home.I also agree with Nathan about taking the first contractor to small claims court.

For pros/cons of booking.com I would say the following...Pros:-if you use guesty you can sync your airbnb info into your booking.com listing info to ease the set up process-there are more options to check off in the amenities portion of the listing set up, so you can really display the uniqueness of your property-I would wager 90% of self-managing str hosts only list on up to VRBO/Airbnb, which means there are not nearly as many options for people to choose between, which means more exposure for your listing-rumor has it that booking.com just invested a large sum of money into building out their services to provide more vacation home listings rather than hotels.