I have no issue with cold calling either.

I spoke directly with Drew Sygit - the founder of LogicalPM and we spent a good portion of 60-90 minutes chatting about the current portfolio, the issues I've faced, and how his company plans to solve it. 

I provide my clients only the number of stamped plans they need (as dictated by the town issuing the building permit) to get one building permit.

The ADU is being promoted heavily these days because it helped government on housing (while they're the one that's causing housing shortage issue at beginning) and at the tail end, they would raise the tax for ADU.So.. if you build ADU, is the house gonna sell more or not ?

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. 

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

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

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.