This gives them plenty of time to search the market.

Be clear about your requirements before inviting them to apply.

Then it sounds like you have a good case but just be cautioned that plenty of good cases end up big losers in court.

Your project manager should know plenty of guys- delegate this to them3.

I believe the housing shortage is a farce - there is no housing shortage - there is an affordability issue and an inventory issue - but there is plenty of housing.

"They are probably in sketch locations"- If by "Sketch" you mean anywhere in the inner city you would be right, however if being in the inner city alone doesn't qualify as sketchy then there are plenty of Section 8 rentals in low crime and very stable neighborhoods. 

Boston should be a great area to expand as there is plenty of investor-owned rental property.

I have college rentals and plenty of clients with college rentals around Seton Hall in South Orange and Maplewood. 

Fortunately, the investors I partner with have plenty of room in their lines of credit to support multiple deals and still have a sizeable buffer before they max out the credit.

(With invested capital, this matters, plenty of people are worth "taking a shot on" in other capacities, just not with respect to managing my money).2) "Is this investment where I'm giving you money the top priority in your professional life?"