The underwriting is based primarily off of the property, not you as the borrower so the main factors evaluated are property value, DSCR ratio (cash flow), LTV, and FICO.Also, I am from Boston and know the area well.

They can help you navigate any potential tax pitfalls and ensure that your strategy maximizes your benefits.Overall, your plan is ambitious and well thought out, but it’s crucial to keep these factors in mind to ensure success.

You're missing one factor: That you can sell your property and probably not pay capital gains since you've lived in the property for 2 our of the last 5 years.I'd split, sell and take the money (or most of it) cap gains free.

But it does not offer that 'wow factor'.

"Oh man, that could have been said differently and he would have more influence and help more people". 

My fiancee has to commute to the loop, which is an important factor. 2.

The 180 day limit was never a factor, even the 45 day limit didn’t come in to play. 

Another factor that is very important is the bidding process. 

However, increasing insurance rates means that this shortage is also increasing so my monthly payment is increasing exponentially to accommodate the increase in both my insurance rate and my shortage (my mortgage has increased over $400 monthly in the past 1.5 years because of these factors).TL;DR - Is it normal for a bank to require a positive escrow balance at all times like my current bank does?

This all depends on the loan factors like Credit score, LTV, DSCR ratio (rents vs the PITI payment), and loan size.Good news rates are down but the other positive news is they are trending down and that means you can pull cash out now and then simply refinance in 12 months or more to lower the rate.