The Advocate - Finance board member sued over plan for new home
Here's the old "waiver and estoppel" argument in a complex factual situation with an old association. Cases like this are tough. If the HOA gives anybody a break, then somebody comes along and says "me too," arguing that the rule is no longer enforceable against anybody. To avoid claims like this, attorneys sometimes advise BODs to never make any exceptions. That often leads to silly and oppressive enforcement practices that end up in the press. Personally, I think boards should be able to waive rules or make common sense exceptions without losing the ability to enforce it later. But that requires courts to do case-by-case analysis that can go either way...
And one the question of building a new home on an old lot, should the old covenants still govern?

"Rubino, an attorney, said the set-back requirements should not matter because his house, built in 1949, is out of compliance now. "Right now, my house is in violation," he said. "It was built in violation . . . as were several other houses." The association has a history of letting the rules slide, he said. "They have allowed so many people to violate the restrictive covenants, they can't enforce them on me," he said. "You can't selectively enforce these restrictive covenants." Among the violators, Rubino said, is [the] association President...
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...and if so, that never looks good, does it?