Here's some more. I'll try to focus in on the 50s for you. Things are actually harder to find for the 60s due to television taking over but I'm sure there's some radio out there.
The entire Quiet Please series, but especially The Thing on the Fourble Board.
Where are you running into the issue, exactly? There are some good programs out there that will do all the converting necessary and burn the CD for you.
If I recall correctly, Infrarecorder is decent: http://infrarecorder.org
One thing to remember, though, is that audio CDs only hold I think a maximum of 79 minutes of sound, so you will probably only be able to put 2 shows on a CD.
Now, some CD players have a data mp3 feature, meaning you can burn a data CD containing a bunch of mp3 files, which can be played, and this will allow you to put dozens of shows on one CD.
If you want some help, feel free to PM me, and I can step you through things. If you know the exact model of your CD player, that would make it easier to figure out the best options for you.
Amazon and a few other places have the 4 movies on one DVD. As far as digital availability, probably not.
I heard this series before I heard Have Gun Will Travel, but Frontier Gentleman also stars John Dehner in a very similar role. It was the first western I heard to take on more serious stories than Hopalong Cassidy's innocuous mysteries.
Listen to it on archive.org or at otrwesterns.com, my go-to OTR resource.
As a big fan of Jack Benny, I always recommend http://jack_benny.podomatic.com/
There is a wide selection of shows and he now has a companion podcast https://www.podomatic.com/podcasts/judy-garland
And the book:
“Old Time Radio Listener’s Guide to Box 13”
I really appreciate everyone's feedback! Does anyone use any vintage radios or vintage radios replicas to listen? I have been doing that lately and I feel it adds a little something extra. I still usually am streaming the content from my phone or computer, but using a vintage style radio/speaker is something I'm real enjoying! Anyone else?
Just ordered - ClearClick Retro AM/FM Radio with Bluetooth - Classic Wooden Vintage Retro Style Speaker https://www.amazon.com/dp/B075MSPD98/ref=cm_sw_r_cp_apa_4UHKAb588VZAD