Board Member receives an expensive perk

Were there board meeting minutes about this? I don't know how you found out, but you might want to read the last 6 months to a year's worth of minutes to see if the work was mentioned before assuming preferential treatment. When was the last time the community roofs were replaced - perhaps this building didn't need it at the time or were recently damaged from bad weather - there may be some information in the most recent reserve study - get a copy and read that too.

Where did the money come from - reserves or an insurance claim? Was the work scheduled months ago and is just now being done because of delays (the contractor's schedule, getting supplies, etc.)?

Go to the next board meeting and ask questions, and bring your neighbors with you so they can hear the answers. If there's hemming and hawing, a flat out refusal to say anything, crickets, people getting indignant, anything except the truth, you and your neighbors will have to decide your next steps (e.g. a special meeting where all of this can be discussed). That may or may not lead to another special meeting to see if this board member and his/her colleagues should be replaced. In which case, you'll need other neighbors (including you) willing to step up and take over. Then you can take a good look at the finances and decide if an audit may be necessary to see if there's been mismanagement or other nonsense happening with the money.

This isn’t a perk. I am on the board of a community that is well funded. The board completes projects based on need. The fact a person is a board member does not mean he has to wait last for services and repairs.

If your HOA is only 37% funded, it usually because owners want the Perk of low fees, which never works out.