Yes, there is easily 10 seasons of cruising from 'Newfound to the Carolinas and further south'. You'll enjoy some places more than others, likely revisit some places, and maybe switch it up and cross an ocean in 5 years or do something different. Going down the east coast
you can stop and fly home when you want, same goes for points south with planning. And ya you can do it in style with a decent Catalina
Cruising the US east coast
gives you wild places, national parks and seashores, historical sites, and large metropolitan areas w museums, shows good food
and booze. If you're interested in all the different options then there's a lot to see and do.
Also there's great opportunities for passagemaking experience. Get some crew or do some short legs on your own.
Whether you will want to keep at it for 10 years or not I have no idea but plenty of people do. And if you don't, you can sail somewhere else, or do something else.