I have some answers (but not the big one).

A “loafer” is an old timey word for tramp, from German/Dutch “landlaufer” meaning “land walker”.

The rest is speculation, but I think this is a sort of anger at nobody returning his umbrella. Nobody does this, which is why this “person” is just a stick. Someone stole Ev’s umbrella and didn’t return it. But you can beat up nobody, so, here’s a literal strawman to beat up.

https://www.barnaclepress.com/comic/Nobody/

Looks like someone had basically the same idea at the same time with another character, only the punchline was that “nobody” challenged the thing instead of Everett (forcefully) doing it

Old Nobody looks like the start of a creepypasta. Like in all aspects of their being. Weirdly shaped, no information, people hostile to it (although this is True, he’s hostile to almost everyone). Just weird!