If you are not bothered about video or TV , There is a version of Android that works well on the Joggler that will give you Google calander , radio apps etc .
Other operating systems that work great are Ubuntu (Linux) this will give you Kodi (Xbmc) etc and is a full blown Operating system : Squeezeplay OS , this works great for your archived music and gives you radio as well as lots of other stuff .
Windows XP will also work .
The above mentioned OS es you download from the software section , extract then write on to a USB stick and they will just boot up from that
There is also a great update to the original OS called PNPIII but unfortunately things on that are starting to stop working now so initially I would try the first things I mentioned .
Post back in the thread for what you are wanting to try and we can help you further .
If the stuff I mentioned sounds daunting , it is not , really

and we all started off like like like like you .
Good luck