Adventurous boomers will like the Caretaker Gazette www.caretaker.org where for over 30 years they have advertised opportunities for house sitting and property care taking all over the world. You pay $29.95 for a year subscription where you can view interesting opportunities that may take you to a ranch out west or a French chateau. The responsibilities involve property and house maintenance plus pet sitting in some situations. The arrangements vary from a free place to live to receiving a salary in addition to rent free accommodations. Many years ago a close friend who was between jobs got an opportunity to property sit for a famous author in the woods of New Hampshire.
 In fact many of the properties listed are second homes and how interesting would that be to stay in the home of someone well known such as an author. There are also opportunities to stay and house sit in hunting and fishing lodges as well as bed and breakfasts where you would most likely meet many interesting people from many walks of life. 
This could be a great chance to experience a different part of the country for those boomers who don't want to be tied down and are looking for a unique opportunity in the world of house and property care taking.