Check out this post: +++ ABBEY ROAD SIDE TWO COMPLETE +++ (OPBk) 2018-03-02 - BEATLES
Phil worked this up using Reaper and I’m sure it took a lot of effort. You could probably do something similar by making each song from your medley as Phil did (one long loop) or each song could be a separate Main Drum Loop. Either way requires a DAW and time stretching. You would be limited to use of a single drum set.