One theory is that the investors see population increasing in these areas and are willing to deal with the ridiculous local laws This actually isn’t even necessary true, the placest with the biggest per capita housing production or “investment” is in the sunbelt, the expensive cities produce a shockingly low amount of housing, obviously zoning laws play a huge role in that as well, but even when you looking up institutional investment in existing properties it’s mostly in the sunbelt, most people who own big buildings in hcol areas just bought them decades ago when they were much cheaper, even D.C. has has like a 4-5 fold increase in value in some areas in the last 15 or so years.

What's your role in the situation and why do you feel so aggrieved by this situation?

I could have easily paid for it, but I did it myself for the exercise.

If you trust your contractor and can stay on top of the project, you might not need a property manager my understanding is the property manager is playing the contractor's role for some smaller projects, not another layer on top of the contractor. 

His criminal record shouldn't play a role if he was released from prison five years ago and has held a steady job, has good landlord references, etc.Disorderly conduct looks pretty minor, and I don't see how it poses a risk to you.

Do you think the high property taxes play a significant role in shaping your investment strategy moving forward?

They make things way too difficult compared to a simpler, DSCR solution.The type of lender also plays a large role here. 

Fast decision-making played a crucial role in this successful deal.

Ultimately, location and demand will play a big role in how it performs.

To recap, you pay to learn the necessary skills to source deals and capital for your educators and  you are actually taught to deceive investors by embellishing your track record and credentials by dangling your GP status in ways not representative of your true role.