I did discuss with my accountant and he is unsure as he is not familiar with IRA rollover process. 

Definitely look at the reviews and ask about their whole process.

And I will state different jurisdictions have different rules, processes, expectations, etc.In my area you are required to have a permit to swap a water heater.

I worked with an expert STR agent, Troy Nowak, who guided me through the purchase and negotiation process.

Im currently in the process of getting it rolled into an actual mortgage since these are rentals.

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

Evan,  As a local broker, I’ve assisted many clients with the entity transfer process, often referred to as a "drop and swap."

Heck, you process debit cards if you insist for 1/10th the cost and non-reversible. 

I truly enjoy the process of analyzing opportunities and witnessing the growth of both large and mid-sized companies.

Certainly nothing ground-breaking in terms of ideas here, however I'll be very hands on (and on site) during the process to make sure that every step of the way is executed to a high standard and very carefully.Once I've hopefully developed a successful track record and gained experience, my next goal would be to move on to commercial assets (think multi-family, industrial etc) so that I can leverage my existing investor network and real estate knowledge to raise 3rd party equity and take on bigger projects.