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.

More over due to fact it's just appreciation/equity play's, adding an amplification to that risk, and now with threats to active income, yet another amplification to risk factor. 

Another factor that is very important is the bidding process. 

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

No one would have factored in a Black Swan event.

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

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?

Now comparing a C class home with a B class of course the C class will have a higher repair factor but that is across the board no matter who the tenant is.

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.