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Yes the rules are vague as the Pyne Ayre HOA's own document states:

"It shall be the responsibility of the Member to assure that all of the rules contained within the Association’s governing documents are adhered to by the Member and any of their tenants, guests, invitees, lessees, sub lessees or any other individual whose presence on the property of the Member or the Association was with the consent of the Member."

Gregory Barry should be familiar with this document since it was revised (which requires a majority member vote) 10 years after he bought his home. If he had a problem with it he's had 18 years to push for it to be amended yet done nothing.

And if following the rules & the "harmony of the community" is really the concern here then why has one of Pyne Ayre's board of directors had a NY state business license for his contracting company registered to his home for the last 3 years when "commercial, business, & industrial use" is prohibited?

From: Short-term rentals ‘not in harmony’ might be denied

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