@redtwo,
You have been a little shy about the setup of your devices.
We gather that you are running out of "Storage" space (Not Memory) on your iPhone and this may apply to your iPad, who knows?
You said in Post #1 -
I have roughly 16 gb of memory but the message tells me I need 26 GB. Even when I remove half of my play lists I still get this message.
It's telling you that you don't have enough Storage space - and removing Playlists won't help at all because your Playlists don't copy music to them - which would take up space - they create links to your music. Therefore removing playlists will not free up any relevant space.
I totally understand your frustration and the desire to tear your hair out over this. That is quite natural; but remember we know practically nothing about your setup.
So please, may we ask you to provide this:
1. Which iPhone, model (eg iPhone 8, x, 11 etc) running which iOS (12.x or 13.x?) Ditto for your iPad. And what is the Storage on these iDevices - eg 32GB, 64GB, 128GB etc
2. iTunes - okay. On which Mac - or is it Windows? We need exact details of your Mac or other computer - Model, year, which Operating System (OS).
3, Following on from that, which version of iTunes? Latest version is 12.9.5.5
Take us into your confidence, please, and give us as much info as you can about all the components in your system.
We are here to help, and willingly, but lack a crystal ball
Ian