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

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“

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

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. 

I am a high-wealth earner with years of employment ahead for me, so I will not feel the weight of this loss other than shame on me for not appreciating this risk better before committing.

I'd love to hear about your experiences—what works, what doesn't, and any tips for making remote property management easier.Most of my clients, including myself when I was an OOS investor, employ a local property manager who already has relationships with vendors / contractors to help you.

I work with plenty self-employed people that qualify in many different types of ways, for different loan types depending on your situation.

That can be getting or job or being self employed/owning a business.

I would only suggest a property management company set up if you are not working for an employer and are interested in retirement account contributions + deducting health insurance costs.If you are already working for an employer who is providing a retirment account plan + subsidizing health insurance costs, in my opinion, no point in setting it up.