@Kashif Riaz for outbound marketing, lead gen and prospecting...

Don't ever worry this much about a single prospect (not even a lead).

What marketing techniques/venues do we use to find prospective tenant buyers who will ultimately be able qualify for a $285,000 mortgage and pay from $1800 - $2000/month lease payments.

Congrats man, it is my hope  to pull the trigger soon, there are a few properties in my Illinois area that look like decent prospects to me.

https://www.biggerpockets.com/renewsblog/20-questions-to-ask-a-prospective-property-manager/

If you're a prospective buyer of a multi-family unit, here's another tip you might find useful when you're kicking the tires on a prospective property.Don't just look at the currently occupancy, check the eviction filings for that property address (it is probably public record at the courthouse - depending on where you're located). 

Just started my prospecting and working out the average operational cost of rental properties in my area.

It has some value, but the prospects of finding a buyer in that market are slim.As the title alludes, would leveraging this land and using the money to purchase local rentals be a profitable venture.

As long as I am happy with where I am today, holding will never make my life worse and only increase long-term prospects for a comfortable life. 

In the past, I've stayed away from partnerships because I have seen them go sour, however, I feel good about the current prospect and can see the value he brings to the table.