Can you help me decide between biting my tongue and saying something in this situation?

You ARE right about the awkward organization of the event, however just don’t bother saying anything. Ask your neighbor to put in the money and don’t worry about it. If it really bothers you, you can briefly mention it to one of the organizers without harping on about it too much. Just let it slide. You could brush over it saying: ” I wish it had been “advertised” differently.

Enjoy it without putting too much emphasis on it.

The only way to have a good HOA is to serve on it yourself.

I think the best way to handle this is via email or a posting on the lake community FB site. I would point out, like you did above, that this is inconvenient for those who work in the daytime, but in the second line or paragraph I would provide suggested alternatives for future events. It may be too late for this event, but in the future… dadadada. If I couldnt provide a viable alternative, I personally probably would not bother with this.

Do a basic cost/benefit analysis whenever you come across dilemmas like this:

The woman in front of you in line at the grocery is spouting divisive, racist remarks. What’s the benefit to you and society in confronting them vs. the possibility of escalating the situation.

The man across the aisle from you on the train blows his nose with his fingers and gets some on your shoe. What is the benefit of confronting him vs the possibility that he may become violent? Can you handle it if he does?

It’s always a good thing to do a cost/benefit analysis in these situations, even something as seemingly trivial as revealing an inconvenience accompanying an invitation to a party. If you merely complain and not provide an alternative, will you be seen as just another crank vs a good citizen in good conscience?

And always accompany your complaint with a solution.

I think you have a valid complaint. I would get someone to pony up for this time but then talk to the organizers or the powers that be to set up a way for working folks to have more time to get their money in.Perhaps a box outside the office where checks can be deposited?

I like the response from @Espiritus_Corvus. A complaint – even a valid one (and this is a valid complaint) – without an accompanying practical suggestion for improvement is just nattering, and of no help to anyone.

But instead of a complaint you could also offer an immediate response to the organizer along the lines of “I would love to attend, and I will certainly pay the fee, but I can’t do it in this short time because…[reasons]. I would be happy to pay you later this evening, or tomorrow [or whenever].” If they have any sense at all, then they can realize – without your having to say another word! – that their planning was faulty, and they need to do better next time.

And if they don’t have sense enough to have that realization without a specific prompting, then maybe you should take over future planning yourself.

Depends how crazy the person on the other end of the message is. If they’re relatively sane, I would say something, but say it in a polite helpful way to avoid coming across as shaming them.

I think I’d say, “Gosh. I would have loved to have attended, but I didn’t have enough advance notice. I hope I can catch the next one.”