I once was a member of a group that met once a month...and each month this old fellow would come and sing "The Strawberry Roan"...to this day, I can barely stand hearing the song!....I guess I am in favor of the longer intervals between doing a song, but I can see that once you get 'famous'....or at least well-known in some group, there will be demand for certain songs.
It is a sad thing, but I am learning fewer new songs lately, partly because I get bored with doing enough repetitions to learn them well!
There is a well-known singer from the UK (naming no names)who comes to the US every 2-3 years, and each time, ¾ of his program is exactly the same....well, done and nice...but, he MUST know more than that!
....and last, I must finally use the remark I failed to think of at the opportune moment: When I first came to this area, I sang several times at an open mic...I was not 'good', but it was a forgiving group,,
..The MC/manager always had a way of saying something nice about everyone, and one night, he introduced me by saying....."Here's Bill Day...I've never heard him repeat a song!"........................and the next day the reply came to me..."Well, Bruce, a song needs some time to recover from what I do to it!"