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Old 9th May 2019
Just a heads up to let you know that the current version of Cakewalk by Bandlab (essentially Sonar by another name but no longer burdened by Gibson ownership -- and FREE!) still has a playlist function. I had never used it in the past but I just tested it now and it seems to work well enough (at least if your project is 'trimmed' so it starts and ends where you want, ie, you don't have unwanted count-ins or dead space at the end).

If you decide to take Bandlab up on the free update/upgrade, I would definitely recommend keeping your old installation and creating a new, CW/BL one. I always did that with previous CW/Sonar updates and upgrades and I was never sorry -- and definitely glad once or twice.