You seem to have all the ingredients necessary to make a go of it: enough money, right age to launch a second career, willingness to learn the business, and enthusiasm. What you will need, when the real bottom comes, is the internal fortitude to steel yourself against the anti-real estate psychology that will prevail then. If history is any guide, the same mass hysteria causing people to defy all logic and buy wildly overpriced properties at the top will be reversed. You will look around you and see the wreckage of years of price declines, and the ruined personal finances of those who took the plunge and lost, and will have second thoughts. I suggest even some current Piggs who are now confident they will jump in at the bottom will really not do so when the time comes.