Once you sleep on the song once or twice the enjoyment fades. Like that favorite song from the radio, you listen 4 or 5 times over several days and the excitement is gone. So you mine as well enjoy it 40 times in a row on day one.
I'm the complete opposite. Playing music on repeat ruins it. But if I listen to a song/album relatively rarely, it feels just as good every time. I also notice new subtle details once in a while, and that makes it even better.
I have songs that I absolutely love and have loved for years now. I just make sure not to overdo it.
Feel like this is probably a better way to manage it if I'm being honest. Actually, this is a bit of a similar way I'd listen to jam bands (Grateful Dead, Phish, Railroad Earth, etc.) Usually too long to listen to on repeat, but interesting enough to listen to many times and pick up on things.
For me, I think short term this is kinda how it works. Although a point I'd make is that is not that I enjoy it less often, it's just that I move onto other things.
Long term though, songs I loop like this can always return and restart their cycle. So it doesn't completely ruin it for me or anything after a few days.
For me the enjoyment fades only if the song itself is not very good to begin with; I start to notice the flaws and after a while I start to hate it and wonder why I even liked it in the first place. Good songs tend to pass the test of being listened to on repeat for me.
In a year or two, that song might be able to bring you back to that point in time. I've started building playlists by the year I discovered the song. It's a trip.