People do it, but my suggestion is to not screw around with federal programs.   

Google Sheets is a great tool for multiple people to track expenses but as they say "garbage in garbage out" so see where the breakdown is and shore that up. 

The title company itself has lawyers and people who make sure you are covered in the legal aspects.

Life is too short to have to put up with these kinds of people in this business, even though this may cause you a short-term interruption in revenue. 

My advice is to connect with right people.

While starting off with this strategy you could also be studying more about value-add options and start attending meetups in your area to get an idea of what other people are doing. 

In the past I have seen the FDIC telling people they will not be able to touch their money for 20 years in such instances.

I think people think of daily and even weekly rentals as truly transient renters, whereas monthly and annual rentals as being more resident based.That said I have seen 14 day minimums and 3 month minimums as well so while by and large monthly and annual terms are common they are not all inclusive.

It's also good to have access to other people who have done the things you're trying to do.

There are many homes in areas outside of Claremont that are selling for $500k to $650k Many of the people we know are buying homes like this one with a construction loan for the ADU ($100k) and buying a home for $700k + $100k : $800k total at 5% down payment and ending with a total payment (PITI) of $6k minus $2k rents from ADU Total new payment of $4k which is easier to make and once interest come down some, they will refinance to drop their payment to $3k to $3,500 per month.