I’m not so sure anyone on the board is lining their own pockets. Yes you should look into it to be sure, but I suspect its more likely one of the following:
(a) A board member who likes to support their friends businesses – in this case, a window company. I sat on a board once where another member consistently month after month tried to get the HOA to switch vendors (HOA mgt, landscaping, repair, etc) to the board member’s friends. I finally had to put my foot down and state the obvious pattern and intent of those requests at a board meeting. Not long after I did that, other board members saw the good ol’ girl (in this case) pattern too and her efforts from then forward didn’t get much traction with any other board member. I think it was a power thing – she wanted to show her friends how much power she had by getting them contracts. I don’t think she would have benefited financially, though I don’t know for sure.
The thing that is odd about flu’s situation is that it would likely take a majority of board members to put out a flyer like that – unless the board is passive and lets one member rule, or unless the good ol’ boy/girl board member had worn the others down with persistent pressure.
(b) The board is worried that the owner-occupancy rate has fallen below 51%. This situation limits the types of loans that can be used to purchase units, and likely impacts property values. It could be the board is trying to spruce the place up to attract more owner occupants and attempting to do that as much as possible on the owner’s nickel.
(c) The board realized that there would be an uproar at the request to replace windows, so they attempted to find a low-cost recommendation for homeowners. At least, lowER cost than what most companies charge.
The only way to sort it out for sure is to get on the board and watch how it works. That is very time intensive by the way. I’ve done it several times and it is such a time drain. I also worried that some of the things the board did would raise legal issues and I didn’t want my name attached to any of that in any way. So I quit being on HOA boards.