It can be done, but it's not fun. I have a hunch you'll get tired of that if you really do it every year. I've taken my 1956 Cessan 172 on many cross countries in 2 years. Indianapolis to Maryland, Maryland to Jekyll Island, Maryland to Nashville, Maryland to Mississippi, then a bunch of shorter ones that are cross country but not super long. By maryland I mean 58M... the far north eastern corner of maryland.
On all those really long flights with multiple refuel stops I ended up with a sore ass, dehydrated, and tired. It can be done, but it can also be done better