Case 1:
Professional couple; no kids, love the ocean/sand/sun. Sold most of their stock portfolio in 2000; bought 3 beach front duplexes from 2000-2003 (prime location). Only deal with summer rental; minimum positive cash flow (less than 2%). But the beach front properties have tripled the values. They got to enjoy all that summer fun!
Case 2:
IT professional couple with 3 kids (all went to private grade schools; oldest one just graduated from Med school). Both left the high tech company in 2000 due to downsize/buyout. Main investment is buying the fixer upper in best school district as rental since late 80th (positive cash flow about 10%). Now they are the full time landlords with 15 properties; the flexable time allowed them to enjoy their kid's activities!