Ask questions to find out about their reasons for selling, desired next steps (i.e. relocation, 1031 exchange, etc.), and anything else that is important to them.Ask follow-up questions to dig deeper and learn more (without being too intrusive) then jot down any relevant notes so that you can reference them down the line during your follow-up calls.

And who better than to recruit a person who is already experienced at such, which there is a lot. 

But mostly keep in mind that any property you find the local landlords already know about and did not desire it.

I live in a very desirably town in upstate NY, refinanced at a super low rate, so will keep the house as a rental.

Desirable first ring city neighborhood. 

I also never had to worry about vacancies: if you own a desirable property, you will always have people lined up to rent from you.

The new design takes the home from a 3 bed, 2 bath to a 4 bed, 3 bath, 2,400 sq ft rambler on a large lot in highly desired area.

There is a mortgage so that also adds to the amount desired, though my inexperienced self still feels it would sell for a pretty penny once fixed up.

Is it desirable? 

But starting with single-family can be a great way to gain experience and confidence before tackling larger deals.If you were someone I knew personally, I would probably suggest multifamily, but it's not for everyone.