Jeremah - First off, congrats on what you and your wife have already built—it’s no small feat managing W-2 income, business income, and rental properties while thinking strategically about tax planning.

I do think the house hacking method will be the best method for me considering I will not be starting off with the biggest down payment.

@Daniel Cisneros No i didn't sign up with him.

We have done this multiple times as long as both properties are rentals it shouldn't be no problem.   

But my gut might be saying no, the following are my thoughts and I'd love feedback:*Not sure a bump from 7 to 9 guests would meaningfully increase nightly rates.

There is NO exception for a 3rd party service that costs more. 

I like Relay, you can have up to 18 checking and 2 savings accounts for no charge, and you would be able to easily connect them to a bookkeeping software.

Do current tenants have a say in deciding if the landlord will be allowed for this conversion or no? 

The place I used provide cost quote and estimated savings at no cost. 

No regulations restrictions, low average vacancy rate.