What are my options looking like?

Sounds like you're in the market for a Samsung Galaxy Player
http://www.samsung.com/us/mobile/mp3-players/YP-G70CWY/XAA

 

Truth be told, spec-wise the new iPod Touch beats this in nearly every conceivable way. However the two things this Galaxy Player has that the iPod Touch does not is a GPS chip and FM Radio.

If you wanted to "escape" the Apple ecosystem and try Android, this is really your only realistic option.

If you're not concerned about apps or taking pictures or other mini-computer features, there are several generic media players you can get for cheap.

 

I have to agree... The Samsung Galaxy Player is THE Android (or perhaps any reasonable) alternative to the iPod Touch. It also depends on what exactly you're looking for. Are you very familiar with Android? If so, check these out also: http://liliputing.com/2011/10/8-android-alternatives-to-apples-ipod-touch.html . Of course, that article is a year old, but I'm sure there are probably updates to those devices. Just to give you an idea... The Samsung Galaxy Player also comes in a 4.0 variety if you are looking for something about the same size as the iPod Touch. Maybe I'm being ignorant, but I thought Amazon sold everything!

 

If you're able to buy a galaxy player, they even have a 3.6 one if you want to go that small: http://www.samsung.com/us/mobile/mp3-players/all-products I love the fact that you can add storage space and I would have chosen the Galaxy Player, but I like to experience a variety of operating systems in my devices. Windows is my preferred computing/laptop device, Android is my preferred phone device, so the iPod Touch will give me the iOS variety. I am also not a fan of Apple especially because of the limits such as iTunes/non-customization etc., but I would like to play around with the new iPod Touch once in a while. It looks great and I would be getting a huge variety of apps this way. Apple, Android, and the new Windows.

 

Now that I'm looking at the players myself, you have me second-guessing too! Galaxy Player: Multi-Tasking, FM Radio, GPS, Microsoft office, etc. starting at $129 for 8 GB which could be up to a total of 40 GB with an SD card. Would really make much more sense, but since my phones will always be Samsung, I guess I shouldn't feel too bad about spending so much money on my one ios device. :/

 

When you say "good", what exactly do you mean? Sound quality? Build quality? Size? Weight?

If you're looking for a pure audio experience, have you taken a look at the HiFiMan HM-801? Plays mp3, wav, flac, ape, aac, ogg, wmv files, has removable storage (SD Card), and even has an on board Burr-Brown DAC and OPA627 op-amp. Completely blows away any other PMP on the market in terms of sound quality. However, it's not cheap (about $800).

http://hifiman.us/Products/?pid=72

 

There is no reason to be disappointed at all. Apple has improved their iPod Touch a lot. In fact, I feel like the iPod Touch was improved more this year than the iPhone was. 5 MP camera, Siri, retina display (same as iPhone 5), 4" screen, VERY thin/lightweight etc. http://www.apple.com/ipod-touch/specs.html So it would definitely be a huge step up from your 2nd Generation iPod Touch. iTunes has also changed a lot; they are coming out with a new iTunes by the end of October (perhaps around the time the iPod Touch will be released to stores). However, iTunes is still iTunes and it will always seem like a hassle compared to the devices that you can just drag and drop everything and not have to convert video files to mp4 etc. I think you can also store your items through iCloud, but I have never used it. To me, the negative aspects of getting an iPod Touch compared to another music player is the iTunes limitation, video converting (a big hassle when converting movies), the lack of customization, and the lack of multi-tasking. However, since the iPod Touch will not be my primary device; I think I can live with all of that just to have the ios experience/Apple app store apps along with Android and Windows.

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Do you want to have an OS on the music player? If you do not need any apps and only want the device for music or videos only; there are a lot of options out there perhaps with much better sound/storage capabilities.

 

You could consider a used Android phone (Galaxy S2 for instance is $200-250 on eBay) or even a new GSM Galaxy Nexus from the Play store for $350. S2 runs ICS and GN runs Jelly Bean (but doesn't have expandable memory).

You don't need a cell plan -- just use it as a media player. They also make great (free) wifi phones, especially if you have a Google Voice number and use an app like Talkatone or GrooveIP. Google Music is pretty darn good -- you can keep 20k files in the cloud, "pin" the ones you want to the device for listening when you're not on wifi, and it will sync happily with iTunes (except for Apple lossless or DRM'd files).

I have an iPhone 4s and an iPad2 so I like iOS too, but Android is great as an alternative and in many ways more customizable if you enjoy playing with and tweaking your device. All the widgets available on Android devices in particular are a step up from iOS. I have a Galaxy Nexus and swap my SIM card back and forth between that and the iPhone 4S (I bought the GN myself -- the iPhone is from work).

 

The Galaxy Player is an interesting option. I actually looked at one the other day. Reasonably priced and love that it has the GPS feature. Only problem with it is that you will need some sort of wifi connection to use Google maps or a stand alone app for true GPS. The other issue that bothers me with this is the fragmentation of the Android OS. But if you are just looking for a music player then this will work.

As for me... I would go with the iPod Touch. Better resale market if you decide its not for you as opposed to the Galaxy Player.

 

The updated Google Maps on Android now has an offline feature that lets you have the map work a whole city offline. Not sure if that would be on the Galaxy Player, though. Also not sure about the GPS functionality; I mean the player does have GPS so if the new Google maps are on there, it should work fine.