We are a commune of inquiring, skeptical, politically centrist, capitalist, anglophile, traditionalist New England Yankee humans, humanoids, and animals with many interests beyond and above politics. Each of us has had a high-school education (or GED), but all had ADD so didn't pay attention very well, especially the dogs. Each one of us does "try my best to be just like I am," and none of us enjoys working for others, including for Maggie, from whom we receive neither a nickel nor a dime. Freedom from nags, cranks, government, do-gooders, control-freaks and idiots is all that we ask for.
The only people I've heard of who do the Loop all at once are recently-retired people who are working on their bucket lists. Like hiking the Appalachian Trail (anotherr common bucket list item), many people do it in stages.
You have to keep a weather eye out on the Great Lakes.
Years ago, I met some people doing the loop. They were retired. I met them in synagogue in South Carolina. They were expected and did a presentation on the part of the trip that they had completed. It was the first time of heard of the Loop.