When EPMD released their greatest hits album in 1999, they had to re-record the songs they wanted to include from their first two albums, because the masters weren't owned by Def Jam.
I don't think it's a bad idea to re-record old songs, especially if you put out the original song when you were really young. You could do it with an improved voice, add some new arrangements, change up some of the lyrics that didn't make sense before. Just don't wait to do it when you're
and don't have the chops anymore.
Also, I know I'm alone here, but this version >>>>>>>>>> the original: