DH and I have done this. When I was single, I bought my retirement home. I could afford it, but I wasn't old enough to live there yet, as it's in a 55+ community. After we married, DH saw the place and liked it. Prices were low at the time, so we bought two more, updated them and rented them out. When he fully retires in 4 years and our other obligations are seen through, we will spend at least half the year there. We will do the big remodels one by one and sell them off. We love our tenants and don't wish to displace any of them, so having multiple houses in the same area gives us lots of flexibility. DH is the kind of guy who likes to stay busy, so we are looking forward to this next phase of our lives. Though we searched actively for 1-2 more, prices have rebounded and they don't pencil out any more. This is obviously a good thing for the ones we own, as rents have ticked steadily upward.