Win ME is basically a suped up version of Win 98, so no, most new software, nowadays will not work with it. I have Win ME & I'm going through the same problem.
The only MP3 player I've found that works with ME AND has all the features I want - capable of making playlists, sorting my own songs vs. shuffling only, is this OLDER model of Sandisk. It got 135 great reviews from
Amazon & other places. NOTE: it is a rectangular shape, NOT the newer odd looking shape out.
http://www.amazon.com/gp/product/B00066EK2W/qid=1133900346/sr=8-1/ref=sr_8_xs_ap_i1_xgl23/102-3449844-6225715?n=507846&s=electronics&v=glance It also comes in the 512MB size.
It was down to $69 on sale with a rebate before Black Friday. I missed the rebate by one day!

Hoping it will go back down immensely after Xmas.
Also note, a lot of sites to buy & download MP3 songs sites do NOT work with Win ME. Itunes & Napster do NOT. So far,
Walmart & Emusic.com are two that I found do. make sure they have the latest version of Windows Media Player, along with the updated codecs, installed on their PC to hear the downloaded songs correctly.
