Tech Really need some new iPod help, reward offered!

I have a very old iPod, about 10 years. A few weeks ago it suddenly up and died, recharging didn't help. I made appointment and went to nearest Apple store, which isn't very near. The young man got it going but I figured sign of the times. These devices are not meant to last forever. So I got a new one, cringing at $200 price tag. I told him I spent a lot of time creating my play lists and want to transfer intact to new iPod. He told me if I have trouble make a "genius bar" appointment and they would take care of it.

Old iPods, you just turn on and they work. I am actually on my third, and previously when I got a new one hooked both to computer, iTunes opened, copy/paste files. Easy. New iPod needed programming. I thought, better have one of their people take care of it. So made a second appointment.

Yesterday back at Apple store. Another person helped set iPod up but said they needed my computer to transfer playlists. I have a desktop. I assumed I could use on of their computers, logging in with my user name & password but he said no. He said he would arrange for me to be called and I could be walked through procedure over the phone. Since he was scheduling appointment I would get a senior advisor.

While waiting for call I took a look at iPod, seems to have everything iPhone has except phone (I really don't need all that, just music). I checked out the camera. Then I couldn't close it.

When they called I explained my issue but said first let's close the camera. She said tap home button twice which didn't work. She didn't know what to do. Obviously not a "senior advisor". I asked for one and after long wait got a tech. He said I need to download new version of iTunes ($200!) It wouldn't download. I get notices of Windows update and usually just do what they call "important". He said download everything. Rather than have us on the phone during download, I scheduled new appointment for Friday. Installed Windows updates, restarted computer, still could not download new iTunes.

So did some checking and realized my iPod is not the only thing that is old. My computer still runs Windows 7. I use it for basic email/internet, Word files, financial records, and most important, recipe files, and it works fine for that. But sooner or later I knew I would have to update. Can't get Windows 11 unless I have Windows 10 and can't get Windows 10 because my system won't support it.

So... unless person with whom I speak Friday can get new iPod working with old iTunes, my options are:
1) Buy a new computer, transfer all my files, buy new iTunes, then finally set up iPod, which by this time will cost about the same as my monthly rent;
2) Return new iPod and hope I can get my money back.

But I know there are always workarounds. They aren't going to tell me them officially.

So, to come to the point of this tale of woe, can anyone help with this?
Pick any kind of cookies you want.

The camera is still open.

 

Is your music purchased from iTunes?

If it it isn’t, I would go with an MP3 player. That way you don’t have to upgrade your computer if you don’t want to. As long as you have your music in a folder somewhere and not just iTunes.

 

I got a 2000 gigabyte external hard drive that you can drag and drop your files onto with usb cord from your unit...then when you get another device you can load it back on

 

Get an MP3 player that isn't ipod?
Some music purchased from itunes, some uploaded from CDs.
When I attach new iPod to computer it doesn't even show as attached device.
Will probably return it.

 

I purchased a Pyle wireless speaker for less than $75 and it has a USB port and a Micro SD slot. It also has a FM radio.
I use this to take fishing with me where there is no wireless. I have several USB sticks with several thousand songs that I can just plug and play on either my old Mac or any devise that takes a USB.

 

Pyle Wireless Portable Bluetooth Speaker - 200 Watt Power Rugged Compact Audio Stereo System - Rechargeable Battery, 3.5mm AUX Input Jack, FM Radio, MP3, Micro SD and USB Reader - PBMSQG12

This is the one I got ....very nice sound and easy to use anywhere. Its rechargeable and last for hours on one charge.

 

Got to the point where I can get both iPods to show on computer but files don't transfer. Getting a call tomorrow. See if we can make it work. STILL can't close the fucking camera.

 

Nope.

 

Are you rebooting it by pressing and holding both the power button and volume down button until you see the apple logo? If not, try that instead of just using the power button. (*)

(*) - I am not a frequent Apple user, so they might have changed the combination to reboot the device, but that's what I remember.

 

It's put away but I will try suggestions
Ridiculous it should be so hard.