Looking for iPod/iTunes alternative

I used to have an iPod Nano for years and really got used to the interface as well as getting attached to iTunes and worked long and hard to organize a massive music library with it.  After about 9 years it finally gave out on me and I replaced it with a cheap little mp3 player not realizing it wouldn't work with iTunes.  And now I realize that pretty much only Apple products work with iTunes but I'm not interested in any of their products.  iPods are packed with all kinds of stuff I don't need and cost hundreds of dollars.  If I didn't already have a smartphone and a tablet I might think it a good investment but I do.  

My main problem is that all of these mp3 players I see as well as any music app I try on my phone all just want you to drag and drop files.  I don't want to go digging through folders whenever I want to take some music with me and more often than not I end up having to go in and re-name all the files just to make albums actually play in order.  Sometimes it mixes them up anyway.  

So my question is, is there not another mp3 player on the market that pairs with an iTunes-like software and just lets you send music to the device instead of dragging files around?  I've tried some apps that are supposed to sync iTunes with other music players but they worked poorly or were lacking in the functions I actually needed.  

Here is possibly an unexpected answer:

Buy an Amazon Echo Dot - instead of finding music, downloading music, transferring music, etc., you can just tell it to play whatever song you want (within reasonable limits - they offer a discounted $3.99 per month for one device for pretty much unlimited commercial music)

It doesn't sound obvious, but imagine laying in your bed and just saying, "Alexa, play Carlos Sanatana - Supernatural" instead - or whatever song comes into your head

If you need it for a car instead of the home - Amazon Echo Auto

For jogging, you are better off using Spotify, Pandora, etc on your smartphone

If you are more into indie, non-commercial, rare music, then you may have to go with another choice.

Here is possibly an unexpected answer:

Buy an Amazon Echo Dot - instead of finding music, downloading music, transferring music, etc., you can just tell it to play whatever song you want (within reasonable limits - they offer a discounted $3.99 per month for one device for pretty much unlimited commercial music)

It doesn't sound obvious, but imagine laying in your bed and just saying, "Alexa, play Carlos Sanatana - Supernatural" instead - or whatever song comes into your head

 

If you need it for a car instead of the home - Amazon Echo Auto

 

For jogging, you are better off using Spotify, Pandora, etc on your smartphone

 

If you are more into indie, non-commercial, rare music, then you may have to go with another choice.

Thanks for the reply.  However I have an Echo Dot which isn't the solution I'm looking for.  I have a large amount of music stored locally that I want to be able to transfer to an MP3 player.  A lot of stuff that's not on Spotify or Amazon Music.  Stones and Pink Floyd bootlegs, some official albums (like live albums and rarity collections) that I can't find on the music sites and stuff like that.  And the MP3 player is for listening away from home, namely my car.  At home I just listen to it on the Desktop through iTunes where I have all that music organized.

Edited by NoCode0680, 12 February 2021 - 09:36 AM.

Im inherently distrustful of non-branded MP3 players on Amazon, but Sandusky MP3 players may be a good choice. It has been too long, though, and I cant confirm that the newer Sandisks will read existing Apple playlists. But it will accept new playlists.

Thanks for more replies guys.  But that's something I ran into with one of the programs I tried on my phone to put my music on it, I don't just want to be able to sync playlists.  Every time I want to put an album on my device I don't want to have to make an iTunes playlist for it.  That's almost as annoying as annoying as having to drag/drop folders and manage file names to make sure they go in order.  Before coming here to ask I did quite a bit of research (plus testing some alternatives) and came up with a few music players that supposedly did that but it's not what I'm looking for.  

It's funny when my iPod Nano died I actually thought they would be cheap as hell a decade later, not discontinued with the only option being twice as much because it has a bunch of features I don't need.  Once I figured that out I assumed that in the past decade somebody has managed to make a comparable or better interface than iTunes/iPod but I guess not if it's all still dragging and dropping files.  I feel like we've gone backwards here in terms of technology, with Apple at least.  As now it looks like my best option is to go on eBay and take my chances on a refurbished Nano or something.  

You could try the programs mediamonkey or winamp. Both let you use the ipod as a MTP device.

Two friends of mine had the same issue, and they moved to the new Sony Walkman. I'm not aware of any iTunes equivalent, but a google search reveals Media Go which is meant, from the description to do something similar (as I understand it). 

Just to let everyone know, MediaGo is no more. Here is a link to a page where alternatives are listed:

https://alternativeto.net/software/sony-media-go/