And than going a level deeper each specific location has different leadership that varies things, and then teams within those locations. 

When you need them to get a contract or disclosure signed, a showing or an inspection scheduled, a walk-through done or a contractor arranged, they're busy at their other job and are unreachable.The only thing lower on the totem pole is Zillow, and that's really saying something.The fact that you're still living with parents and can tolerate the startup (no income) phase is solid gold.  

ensuring the condominium was properly created, the condo association has competent leadership & is properly funded, the condominium has strong declarations/rules/regulations that are enforced, etc. are important due diligence questions. 

After that, it's a guess, but I think things will swing back around to this part of the country at some point.This part of the country suffers from high taxes and over-regulation, and demographically people (especially older people) and companies have been moving to other parts of the country, as you noted.I think it will take a lot of time, and a change in political leadership (probably several changes) for there to be a will to make our part of the country competitive again, for the tax burden to businesses and individuals, but I think it will eventually happen.There could also be some change that we can't even foresee yet, for example maybe in 15-20 years climate change makes the southern part of the U.S. a lot less desirable than it is currently, making the Northeast look better in relative terms, right around the same time (hopefully) we get new political leadership which tries to lure individuals and businesses back from other parts of the country.It's hard to predict that far out into the future, but again, things tend to happen in cycles, so while I would never recommend anyone move to the Northeast right now, if you have to be here for some other reason (e.g., family), I think the trend will eventually swing back in the Northeast's favor.

I'm assuming this is a solvable problem, but it still bugs me that my tenants (4 girls) still have to live through this.My greater concern is the interelated combination of three things: HOA has ZERO reserves, the Board is providing minimal oversight/leadership, and the property management company is lousy.

The NAR leadership is in flux and members are dropping out.NAR President Warns DOJ A “Bigger Problem” Than Sitzer/Burnett (therealdeal.com)

That starts with leadership at that company you select to protect your investment.  

As a student of Organizational Leadership and Developmebt I’ve spent 10 years looking for solutions.

Things like retirement, home ownership -- all of this can be attributed to government leadership.

Through this I had leadership training and better still real world experience on how to run a team, I feel people under me like working for me and I am very strong at coaching/teaching (forward movement for all).