How might it work for: a)Team with low stake 1-2% that are staying b)Contractor from early days that was compensated with 1% equity c)Investors with small stake e.g. 1-2% Do they typically get half now, half later or do they get lot on sale?
Next time, get this stuff figured out at the start and written down in your Operating Agreement. The OA tells everyone what the agreements are on how things like this will be done.
You may be able to do that now, but it's going to be more challenging to get to consensus today. You're pretty much guaranteed someone is going to be unhappy with the results and that's going to cause trouble.
Minority shareholders have rights. Learn what those are.
You need to talk to an attorney and an accountant now and get their "professional advice." I am neither of those and this is not "professional advice."