Legal Question in Business Law in California

The answer to question #1 is "probably yes;" provided the deals don't adversely affect any stockholder of one corporation who is not also a holder of the benefitted corporation and all the details are known to him/her. The answer to #2 is "probably no" because the rules regarding the organization, purposes, use of income, etc. from non-profit corporations probably conflict with your intended use of the non-profit. A more complete answer isn't possible without more details regarding the ownership, management, purposes, etc. of the proposed corporations.

Actually the answer to both questions is, "Yes," as long as the structure you are proposing is not being done to defraud anyone, or evade taxes legally owed. The other limitation is that the non-profit must have a substantially higher percentage of "disinterested" directors than directors who do business with or work for the non-profit. I don't remember the exact percentage, but it is more than just a simple majority. The disinterested directors must make sure that the transactions between your for-profit corporations are arms-length and in the legitimate best interests of the non-profit.