@Carlton Bynum - to your list I would add to check: gutters and downspouts (especially since the bottom of the downspouts might be buried in over a foot of snow); heating system air intakes and exhaust openings (with direct vent units these are close to ground level and could get buried); nearest fire hydrant being accessible in case it is needed (snow plows tend to bury them).

Is there any merit at all in taking one day (Friday) and seeing if I can convince him to move out on his own?

I've called other places to manage the building, but since it's in a run down part of the city, they were not interested in taking over the management.  

This should help you figure out just how many eyes look at the property, which you can then use to calculate the 'follow-up' rate, when you actually get an email from a person interested in taking a look at the property.

Hello, My name is John Beasley and I am interested in taking the steps the learn the industry and start my path to investing.

I am also a physical, hands on learner so I am also interested in taking meetings or calls to learn more about the business. 

If you are interested in taking a more holistic approach to personal development, I would suggest Radical Acceptance by Tara Brach or The Four Agreements by Don Miguel Ruiz.

., always keeping them in the same room she is in, taking them outside every 45 minutes, etc.)Curious what everyone thinks about this situation, and is it worth it?

Now, with starting my search for a multi family to live in and rent out the other half, we are always reacted to the seething, or sharp breath intake about moving there.

Automate it fully.As far as marketing, make sure you have an intake form on your site, build your credibility, work on your back end systems and processes and make sure you're ready to scale.