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.

What about something like this: https://www.realtor.com/realestateandhomes-detail/3032-Glenm...?

Are their listings detailed with good-quality photos?

Also I have not worked out the financing yet. if I just use my cash then the Cash on Cash drops to 8 or 9% and that would be below my Cash on Cash target.Generally speaking and of course just numbers I picked out of the air for reference when running numbers in my head, I am looking for Cash on Cash greater than 15%, high probability of long term occupancy, and no expected major Capex for 2.5 years after purchase and purchase time repairs which I would add into the cash on cash evaluation before pulling the trigger.So there are some more details to be worked out in my head but being it is my first one and only learning what I could from youtube videos I thought I would get some feedback.With all that said, in my head it seems like it could be a good start.Thanks again Jaycee and Gavin for your feedback.

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!

The key is doing good analysis on the rental market and finding a good property manager. 

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.

Quote from @Chris Clarkson: Initially I’m wanting to start in the local Chattanooga/North Georgia areaWould you be interested in something like this: https://www.realtor.com/realestateandhomes-detail/3621-Missi...?

I've been doing some analysis on AirDNA and it's saying the general area is a good investment for STR.

Are their listings detailed with good-quality photos?