The following commentary comes from an independent investor or market observer as part of TheStreet's guest contributor program, which is separate from the company's news coverage.NEW YORK ( TheStreet) -- Q: My brother and I have always been close. As adults; I have become financially successful and he has struggled. He has often asked me to lend him money for a variety of reasons. I've always felt obligated to him and have loaned him the money. Recently he asked me to finance a project of his as an investor. I am very wary of this plan and feel uncomfortable investing. I would like nothing more than to trust him here, and yet my discomfort reigns. Please advise me on how to proceed. A: The financial generosity is admirable. However, it is creating an unhealthy family dynamic and cannot continue in it's present form. Follow TheStreet on Twitter and become a fan on Facebook. This "unjustified" obligation toward your brother is breeding "justified" resentment. "Investment" in his projects brings with it obvious concern.