On termination of the tenancy, property or money held by the landlord as prepaid rent and security may be applied to the payment of all rent, and subject to a landlord's duty to mitigate, all charges as specified in the signed lease agreement, or as provided in this chapter, including the amount of damages which the landlord has suffered by reason of the tenant's noncompliance with section 33-1341.

It seems like MA encourages (and maybe even requires) that you register with the Department of Revenue which leads me to believe it should be held in an LLC or business. 

We started a local art gallery and held events like weddings and other entertainment.

This property manager can be held liable for anything that is related to your property from the City. ( Making this position extremely hard to fill).

How have they held up over the years?

Once the auction is held, the person who applied for the treasurer's deed will have the option to match the winning bid.

There are very few banks out there that will allow a seller held second without you coming out of pocket or using some sort of collateral.  

The payment processor says they have no funds "being held" but yet I can clearly see the money was sent and their is a Amex case number that says the money was sent back to my account. 

Not a penny paid to us in the 2.5 years we have held this, and now we are looking at a loss of some of our capital. 

Sorry (not sorry) for the bad PR Schultz, but you need to be held accountable.