Any recommendations on a professional with whom I can discuss these intricacies in more detail...?

As for the bond IMO all the intricacies get booked on their books - you only care about that you have rec’d an asset to hold in tryst for someone else. 

I don't know which that is for you given the intricacies of the relationships, but good luck!

Just my $0.02 after having been a part of/observing all of the intricacies of thees types of loans a few times annually.

I think the tough thing is knowing the intricacies of different states when it comes to insurance, property taxes, local management fee customs etc.

There can be a lot of generalizations made, but I'm sure even you know in your market there are intricacies and you should work with someone who knows those intricacies.  

Upstate NY is a very large geographic area, and I don't know any lawyer whose business model would cater to the intricacies of all of the municipalities and counties of the state, not to mention the hours of driving to travel to those proceedings.

At least 750 hours in real estate trades or businesses in which you materially participate and more than 50% of total hours in real estate trades or businesses in which you materially participate.There are intricacies beyond the bold face though....Hours spent as an employee in an RE trade or business don't count towards the RE trade or business hours unless the employee is at least a 5% owner. 

As a good management company we will know how to get around some of these intricacies so we can help our investors bring up values in their properties. 

You know the intricacies of your unit and are in the best position to compare.