Our firm actually does no small amount of work with private equity firms that buy NH based businesses... and then don't want to deal with the NH tax issues and farm it out. 

Either way, it's not "easy".The main issue with finding the deal first and raising money later is the consequences of not being able to raise enough money.

My condo association is small and we do allow short term rentals so that is not an issue. 

The ones that went badly were when a tenant met the inspector at the building (without our knowledge) and created issues.

With DSCR loans, none of the problems you are facing would be an issue.

Consider including clauses for subleasing, as college students may need to find replacements if they study abroad or graduate early.In terms of management, be proactive in addressing any maintenance issues and establishing clear communication channels with the tenants.

Building the homes on shovel ready lots won't be an issue to find lending for .

Be prepared to explain your issues and why it did not work out.  

Where you can run into issues is pet urine.  

If you are working with a large PM company and you have an issue 9 times out of 10 you have to go through a hotline to call.