Lots of people have pools here.. depends more on income, yard size, children or if you want the hassle of upkeep for as mentioned depending on the year a four month season. Is it the south or southwest where I guess one can swim outside all year year? No.
Is Cincy really 10 to 20 degrees colder than Lexington? There might be days where it seems that way but on average that is hard to believe as they are only about 80 miles apart. Toledo or Cleveland? 10 degrees maybe.
As far as good rides are you just looking for scenery or places to go? Knee dragging or upright? It is pretty flat excluding SE OH, not Florida flat by any means but there are plenty of nice places to go and roads to take.