A little bit of goofy fun goes a long, long way. Less is more.
There a lots, millions, of actual businesses trackside in this country many with very lovely signs, logos, and names which could fit almost any layout.
Sadly, I have seen far, far to many layouts with joke after joke -- half dressed gal in the window, topless bar with a colorful name, sewage company, etc. After the first time they became really boring and took away from the layout. Like hearing the same joke told poorly over and over.
Amen. I know some really good layouts which have goofy names for every business. To me, that detracts from an overall good modeling job otherwise.
Growing up, I kept hearing about how amazing John Allen's G&D layout was. I was impressed with his scratch-building for structures and his scenery was impressive in its scope and size, but the whimsy? That turned me off very early into my interest in the hobby.
Another thing that annoys far more is that so many businesses have massive signs, and almost always in the Helvetica san-serif typeface, regardless of the era. What is it with model railroaders and Helvetica? I get these signs are so they can be read from a few feet away, but you're not likely to find such a large sign in real life unless it's a very large building to start with. Billboard signs on the side of buildings aren't so common in real life but they're the standard for model railroads.
One structure on my own layout has a O scale sign that you'd have to get just a few inches away to read it at all.
On30 has become a joke among many in the hobby as it's largely a 'catch-all' gauge for all the whimsy you can pack into a layout. Structures that'd look odd in a Hobbit movie, curves that are so tight that they'd look off in Z scale, and cars so short they really should have a single truck underneath them. All are common in On30. I have been told in person and via email many times from people who are surprised that my layout lacks that "amusement park-esqe" quality that so many On30 layouts have,