In general medical professionals are looking for smaller units (studio/1 bedrooms) not 2+ bedrooms- In order to understand corporate demand you should research the types of corporations in the market and figure out if they bring traveling / temporary workers to the area because not all corporations do- You didn't mention colleges but if there's higher education nearby this can also be a driver of MTR demand.

Great area, especially with a college nearby.

He owns another nearby property that is up to date on taxes and well maintained.This particular property, however, is in a dilapidated state and has a city order for demolition.

Is it based of similar properties near by that are for rent or are the lenders somehow able to find out what similar homes that are alike it are renting for?

Since you said you haven't bought your second property due to "risk averseness, lack of capital and analysis paralysis", then I would go with the fewer paid off properties approach.Paid off properties are risk averse because of the large amount of equity and cash flow.

Hi, I'm considering buying a property and would like to connect with fellow hosts in the area. Airbnb offers a messaging option, but I'm unsure if it's appropriate to use for this purpose.

I would suggest that you focus on buying fewer but better properties. 

I see plenty of listings in cities that show the rates for nearby parking lots. 

Even if it’s outdated, you’ll likely find fewer headaches.Think long-term with leases – If rents are below market, that's just room for growth.

I find that when I allow pets, I get more and higher quality applicants who earn more, have better credit, and have fewer background problems.