Here is the only way it would work.
We would need:
-Media person to present our complaint to the public, explain what the issue is. Perform press briefing during the event. Come up with slogans ('Mr. President, Give Us Back Our Freedoms!' or 'Skies', if you will).
-Flight logisitics person to arrange staging airports, ingress and egress routes, fuel, comm etc.
-Safety person to oversee and brief pilots all aspects of the flight*
-Attorney to cover legal issues that may arise, or decide the best way to minimize such problems in advance.
The flight would be well-advertised, not a secret. It's a media event, not a surprise attack. It would be conducted in a manner that does not pose a risk to any flight......especially airline flights. ATC, TSA, & Airforce would all be advised in advance of when, and what our route/altitudes would be.
The flight would trim a small edge of the TFR, not penetrate deep into class B/C, or fly over either the CB/CA airport, or associated USAF airport, or the actual location of the VIP.
*One screwup (nmac or worse, even an off-field landing) would be disasterous to our cause.
We'll call ourselves the TeaPartyPilots or something.
You are either in, or you are against freedom.