This is sick - I happen to run a site for DIY and community organizations like yours. We have proven the best way to fundraise is to throw events like you did but to upsell people on a recurring donation when they get the ticket.
On the off chance you are throwing another event, I would love to help you raise much more than $800 one time (my site is https://withfriends.events/)
Short answer is I would just recommend one of the tons of tax software out there specific to LLC, individual, 501c3. My site helps with the raising money part and just integrates and gives advice for that
If you read what I wrote, it doesn't even need to actually be 5 years if the person does some creative stuff with options which I have personally seen.
There's no legal 'creative stuff with options' to get around the five-year holding requirement. QSBS can be rolled over into other QSBS without restarting the clock, or you can agree to delay the actual sale (including payment) until you've met the holding requirement. At the end of the day, though, you have to hold the stock for five years, and any early payment you take (e.g. for writing options) is taxed normally.
I wish. I know several people in person who do this. Read some of the other commenters saying how this is their standard mode of operation and they don't see any problem with any of this.