Meghan,I insure several 2 unit Condo Associations.  

I know we can get some market research like state-wise from the Realtors association (like this one https://www.njrealtor.com/research/), but if I want to go deeper and understand the market in a county or even in a specific city, where should I go?

Since my first double in 1999, I have gotten my NYS Associate Broker's License & acquired a few more doubles as rentals & done a few flips as well. 

Also, I realize there is a lot of cost associated with sell and buy of another property that would cut into profits, but is the any other benefits. 

I have seen firsthand of bidders bidding on 2nd liens and homeowner association liens on properties that have a 1st mortgage and on partitions of a property. 

@Douglas T.If your condo community is an association then I would assume the Bylaws address the issue of insurance.

As far as I know an HOA board can hold as many meetings as they want but they risk the rest of the association turning on them.

Check out your local real estate investment association.

If you were to value this investment, you would have to base it on a forecast and discount it for the risk associated with hitting the forecast. 

This has defiantly been frustrating.From what I can gather the home owner made a payment directly to the bank at last minute along with paying all other associated court and lawyer fees.