Great post!
This question is the reason why I went to a hard disk playback setup. A playlist is such a better answer than just a single record. My fall back playlists are sorted by genre (blues, pop, rock, etc.) with each song rated 4 stars or better. Each list contains at least 500 songs and it's set to random play. Here's the most ten recent songs played from the Jazz Vocal playlist:
They Can't Take That Away From Me - Ella Fitzgerald & Louis Armstrong/Our Love Is Here To Stay: Ella & Louis Sing Gershwin
Let's Call The Whole Thing Off - Ella Fitzgerald & Louis Armstrong/Our Love Is Here To Stay: Ella & Louis Sing Gershwin
It Was A Very Good Year - Frank Sinatra/Sinatra At The Sands
Fools Rush In - Frank Sinatra/Nice And Easy
I'm Glad There Is You - Sarah Vaughan/Jazz 'Round Midnight
All Of Me - Lester Young w/ Billie Holiday/Lester Young Story: Afternoon Of A Basie-Ite
My Funny Valentine - Luqman Hamza/With This Voice
All Of Me - Billie Holiday & Lester Young/Complete Billie Holiday-Lester Young 1937-1946
Rose of the Rio Grande/St. Louis Blues - Duke Ellington/Duke 1940 Live From the Crystal Ballroom In Fargo, N.D.
September Song - Sarah Vaughan/Sarah Vaughan