Frequently we are asked about either inconsistent association documents or advised that although our documents say X we have always done Y so won’t our past precedent control? The answer is NO.  Your documents control.  You must follow what your documents say, unless there is something in them that is illegal or against public policy. This same point is continually stressed by the courts around the country.
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Harbour Island Condominium Owners Association, Inc. v. Alexander, No. B285755 (Cal. Ct. App. Jan. 24, 2019)

Summary

In Harbour Island, the Court of Appeals of California held that tenants renting a unit that was part of a condominium association did not have standing before the board concerning meeting attendance and fines imposed for violations. The association did not have to give the tenants an opportunity to be heard, unlike the rights of actual unit owners.
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Some states have statutes that require that Associations provide a notice and opportunity to be heard to a resident before the Association can fine them for a violation of the governing documents. Even though Wisconsin does not have such a statute, providing residents a notice of the alleged violation and opportunity to give their side of the story is an important component of providing due process—which will help make your fines ultimately enforceable.
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An owner violates the rules. The Board assesses fines to the unit owner.  Will the fines hold up in a court of law? In this case, they did—and your Association can take note of what this Court says the HOA did right.

Facts.  In a 2017 case, an owner who lived in a subdivision with an HOA planted bamboo in their yard, which then spread and infested a neighboring owner’s yard and some common areas.  When the owner failed to remove the offending plants after notice, the HOA Board started to fine the owner, rather than to exercise “self-help” and take care of the bamboo infestation for the owner. 
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In a 2017 New York case, a dispute arose over what authority the Association had to perform landscaping maintenance on an individual homeowner’s lot (Minkin v. Board of Directors of Cortlandt Ridge Homeowners’ Association, Inc., 149 A. D.3d 723 (2017)).  When the owner refused to pay the assessment for the landscaping services, the Board started assessing fines.  The owner sued the Board.  The New York Supreme Court (the lowest level court in New York) decided that the Board did have the authority to perform the landscaping services on the front lawn and the homeowner was required pay the assessment as well as the fines.  Unfortunately for the Association, there was also a larger issue dealing with the work performed and assessed on the side and rear of the house.  The problem was that the Board and managing agent could not provide backup or evidence for exactly what work was done in each area, and accordingly, the assessments and fines were not upheld in those areas.
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A recent New York Court dealt with an issue on leasing (Olszewski v. Cannon Point Association, Inc., 148 A.D.3d 1306 (2017)).  The Board adopted rules and regulations that placed restrictions on leasing that contradicted relevant portions of the Association’s Bylaws.  The Association then fined the owner for violating these restrictions and the owner sued.  The owner won at the circuit court level and the Association appealed.  On appeal, the Court again ruled in favor of the owner, upholding the trial court’s decision.  Why?
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A Maryland Court recently ruled on the extent of powers a Condominium Board had in dealing with a unit owner who was delinquent in assessments (Elvation Towne Condominium Regime II, Inc. v. Rose, 162 A.3d 1027). The Association at issue adopted a policy by which delinquent unit owners would be deprived of their right to enjoy certain common elements – namely the pool and parking of the Association. When they suspended those rights for the delinquent unit owner, the unit owner filed suit alleging the policy was unlawful, since the Association’s declaration did not provide for the Board to withhold common element use rights.
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A Court in Arizona recently provided one more reason for your association to have a fine schedule and late fee policy (Turtle Rock III Homeowners’ Association v. Fisher, 2017 WL4837821 and 2017 Ariz. App. LEXIS 187). This particular Homeowners’ Association (“HOA”) required their owners to maintain their property in various ways relative to cleanliness and attractiveness, via the HOA’s declaration. The declaration allowed the HOA to assess daily fines if the violations were not corrected. The HOA sent a particular owner 90 separate notices but started fining the owner less than 30 days from the relevant notice.
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An association in southeast Wisconsin consists of plots of land upon which the various unit owners can park a mobile home or trailer. Under the association documents, unit owners cannot be in the trailer more than 60 days between October and April or a $10,000 monthly fine will be assessed.  A unit owner owed more than $13,000 in fines in addition to unpaid monthly assessments.  When the unit owner continued to refuse to pay, the association started foreclosure on its lien. 
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Those of us involved in condominium management, whether as board members, officers, property managers or attorneys, know that VRBO and AirBnB have changed the way units are rented. Short term rentals are viewed by many associations as a problem that should be solved.  Specifically, these associations and managers would prefer that short rentals (most often defined as less than six months or one year, but I have seen it defined as less than 30 days) be prohibited.  The problem is getting enough people to agree on the various issues:
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