Some have seasoning requirements, others do not.

Our area is not unique, this is a nationwide issue (opportunity) for accounting firms.In the end I think many would be well served to think of their CPA/EA as they do an attorney - while they can also help provide planning advice to better structure your tax life and save some money, a portion of the cost is just a cost of doing business - you are required to be compliant by the Feds / states / etc, and the CPA/EA is insurance to ensure you get it right and stay out of their way.

When looking for a SFH there's several factors to contribute to a great rental rate: Location, Condition, Time of Year, Functionality, City Cert requirements needed (if applicable).I absolutely wish that I could 'Turn back the clock' and do house hacking and jump into real estate investing that way...so many great benefits!

Mind you, most townships are now requiring owners to apply for Conditional Use permits along with the STR permit. 

@Margarita Artiushenko knowing the numbers and understanding investing requires risk taking.

It's more difficult now to leverage strategies to take advantage of low down-payment owner-occupied conventional mortgages such as house-hacks, live-in flips, etc due to DTI requirements. 

A house lift and new foundation is required and was quoted at ~170k plumbed & wired, but not finished.All that said, I appreciate you walking me through the numbers, I wasn't sure how to apply these equations to our situation.

You may have to send USPS certified or post on door stating rent increase beginning x date, mine usually includes an addendum extending lease term one year at x rate requiring signature.

This will be a requirement of this proposed settlement.  

I bought the property for the residential units, but there are a couple small commercial units as well that the town requires are used for a commercial purpose.