@Alison CromwellIn order to obtain a flip loan with no consistent income history, the following steps need to be undertaken: create an impressive credit score, put aside more funds as a down payment, check out new methods of getting funding besides what is available from banks or other financial institutions, involve yourself in investments with toughened entrepreneurs, show how financially sound you are by doing things such as getting enough money into savings over time through frugal living habits or accumulating valuable assets that can be readily converted into cash when required among others like developing several stable sources of income or steadily growing one.

How long do you plan on holding and what’s the requirements to renew the land lease?  

Some have seasoning requirements, others do not.

To me, there's no comparison when it comes to complexity and required involvement between the two.

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.

Fast forward through some vital life experience, I’m back on BP with a desire to jump back into my goal of having a cash-flowing rental portfolio that can help support me.

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

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. 

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

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.