@Jaycee Greene yes I am looking at 535K@Kimberly Venable How about a duplex like this: https://www.realtor.com/realestateandhomes-detail/685-W-1850...?

Keep in mind my comments were given with only knowing the details you provided in a post so I don't want to come across as a know it all. 

I'm currently in the process of gathering more details from my property manager.

Will follow up to get more details on your idea!

I'd also walk through them once the tenant is out to see what shape they are in. 

I’m concerned mine is not detailed enough.  

I will not comment as to the tax laws and underlying rules - that is a discussion you can have with your tax advisor who presumably you are paying to help you.What I will do is provide practical and business guidance on tracking time.Firstly, there are apps available that can assist with time tracking where you can specifically detail your time, who you met with, etc.

Maybe you saw this from the Tico Times already, but it lays out mostly depressing details on getting a mortgage in Costa Rica: http://www.ticotimes.net/realestate/25-mortgage-ti...Please post back here if you find anything!

Not to mention, they weren’t aware of my entity information and other organizational details I’d previously sent (ie state formation, scope of work, etc.); easy stuff.

I detail here how my first flip essentially bankrupted me which resulted in this house losing money as well.It’s easy to blame others for all that went wrong.