[jpdoctor]

First, I am not knowledgeable enough to provide advice.

With that in mind: My experience is that it makes sense to go the 83b route before any funding rounds (when the price is 0.001 $/sh).

After that, there is usually decent money going out the door to the IRS. Since such a tiny fraction of startup shares are ever worth a damn, it just isn't worth the time, money or hassle.