Make sure you ask about employment on this form, as this information can help you determine which tenants may be able to afford a rent increase and which tenants may not.

Maybe they will get some family support or maybe eventually she will have a new significant other with good employment that will move on.

To provide an example, I was previously employed in the legal department of HHM, which at the time was a an affiliate management company of a publicly traded hotel development/operation company where we managed  the portfolio of  hotels as well as provided 3rd party management services.

I was under the impression that bank statement loans are an option for self employed

Cities like NYC and Boston have so many employers and infrastructure that one or two major employers can go under and you wouldn't really notice. 

My DTI was borderline with my wife not employed but having friendly bankers on my side did it.

We will be showing material participation so that we can deduct from our W2 employment.

He specifically mentions ”make sure you do not provide substantial services so that you report the STR rental income on schedule E not C and so you are not subject to 15% self employment tax“

New London, CT is by no means a huge city and I am very hesitant to even consider buying real estate around here but the one thing that really keeps me coming back to it is my employer.

I hate to say this because i am totally against it, but you can borrow from friends and business associates, try and find aomeone who can contribute not only funds, but also strategy (since you're new).It's great to have lofty goals, just remember you need to find a way to pave the road to your end goals.