I'm not sure I understand this:
02. One w/CD to download studio to my desktop to work within (before transfering files to MP3 player)
do you mean something with a software to make selections of the files you want to upload before you plug the thing to the pc?
---leaving that aside---
If you want something CHEAP (but still pretty decent for "normal" usage) for on-the-go listening nothing can beat Sansa clip + .
You can use Rockbox with it, compatible with MP3, WMV, secure WMV, WAV, FLAC, OGG Vorbis and digital audiobooks, with sd card for additional storage.
http://www.sandisk.it/products/music...us-mp3-player/
well within your price range even with added sd card to expand capacity.
Only qualms, UI not as "smooth" as other brands/models, feels a bit plasticky...
If you're willing to save a bit more to actually get something more, Sony AS15 is the player I'd buy right now.
http://www.sony-asia.com/product/nwz-a15
(disregard all the pointless mumbo jumbo about its ability to "restore" mp3s quality, it's just a NICE player with good components even for "hi fi" files and reproduction), imho the sweet spot between portability and quality.
but if you listen to music with a stereo system while at home and need just something as "soundtrack" while you're around it might well be a bit overkill.
can't help about the "where to buy" section
...