Your question about a home owners association and HOA assessments raises a number of important issues that may be of broad general interest to readers of this site. I have been representing clients on both sides of real estate issues in Maryland and D.C. for over 20 years.
Commonly, the rights of a condominium “regime” to impose fees on the owners are set forth on a document recorded in the land records of the county where your property is located. Commonly, there is a reference in your deed to where that document is recorded. Sometimes there are other documents that make the homeowners responsible to the HOA and some documents can bind you that are recorded but not references in your deed. There are also county specific laws on HOAs. All these could alter the below.
You mention that Twelve Trees Association accepted and cashed every check. Under Maryland “payment law”, absent an agreement with the HOA to let you catch up, the HOA can generally accept checks and simply apply them to your account without being bound to let you catch up. Maryland payment law and Maryland’s Uniform Commercial Code allow you to take certain actions with your checks and other payments that may give you some control over how your payments are applied.
Since the HOA accepted the checks, it must at least give you credit for each of the payments you actually paid. Whether this was communicated to the lawyers or not, the lawyers must generally also credit you with the payments, as agents of their clients.
If the HOA is not bound to a deal with you -- by agreement, endorsement, contract, law, etc. – then so long as money is owed, the HOA can still seek to run legal fees.
However, Maryland’s highest court requires that attorneys fees be reasonable in comparison to the amount sought. See a Maryland State Bar Association article at http://www.msba.org/sec_comm/sections/litigation/newsletters/LitigationJan2012.pdf. See also the cited case of Monmouth, 416 Md. at 337.
There are state, county and local assistance programs that might provide financial help that could free up other resources of yours to pay off the lien.
Of course, other factors can also intervene that would alter the above. This response is not intended to address all possible issues.
This is at best a general overview. I encourage you, and all other readers, before you act (or decide not to take some action) to seek competent, local legal counsel who can address the specific facts of your particular situation.
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