I've had a couple of people suggest to me to 1031 exchange my SFH here to buy multi-unit OOS or many SFHs...sounds like huge headache venturing into the unknown and all those tenants, repairs, capital expenses etc. 

Whether it's an electrician, or yard person, title company, Property Manager, etc. usually getting a referral from another investor in that market helps limit our risk to "unknown" people. 

Basit-  The point of the podcast that I was listening to was that this "STR Loophole" ( I know it's not a loophole, but that's what they were calling it on the podcast) is relatively unknown to many tax professionals and STR owners.

She might not qualify for another loan, unknown it depends on if she can show it as positive rental income but with your plan it sounds like she won't have tax returns in the future to make this work. 

It was more of a general example of unknowns I will encounter in transitioning my primary to a rental property.

However, the site work is going to be a challenge to price out since there are many unknowns.

I don't want to stockpile cash in fear of the unknown, but I don't want to start over financially if the worst occurs.  

There are always many unknown factors but I will tell you my most recent property was a bank owned rental property they tried to rent it for $2,000 then dropped as low as $1,750 but when I purchased it I had multiple section 8 parties interested at $2,100.

Thanks for sharing @Anton IvanovI have great respect for people with passion, goals and "right" mindset.Your post demonstrate perfectly what can one achieve even with many unknown variables (remote markets, using teams over self-work).I have much to learn and your post gave some great ideas and especially ambition to pursue my REI goals.Have a great day,Benny

I also had a green tag on the garage permit and thought that the certificate of occupancy was for the entire project. at which point I put the home for sale, only to learn that the permit for the garage portion did not have a final stamp of approval when contacting the building department, I was told by the manager he would not allow an inspection on the garage permit that I had not completed the variance process and would need to revisit the entire process in order to receive a final inspection on the garage permit . there is a lot more to the story than I would like to put here but I feel I am being wronged by the manager of the building department for some reason unknown to me.