My best friend at work wants to rent my RV for an extended road trip across the USA. He will be gone for two months or longer. I figured this is a good deal for him and an opportunity for me to recoup some of my expense of this toy. Will my insurance cover this exposure?

Look very carefully under your automobile policy exclusion provisions and you will find very emphatically your automobile insurance will not cover any vehicle rented or leased to others. Don’t take the chance of saying, “well I’ll just let him borrow it and then he can voluntarily pay me later.” Instead, have the friend go to his agent, add it to his policy under a trip permit and add you as additional named insured so in the event there is a claim his insurance company will cover the physical loss and then represent you if there is litigation.