Setting up Homegroup/Workgroup Issues

Hello,

A little back story before I address my problem. I have an older desktop running WIndows 7 Pro 64-bit I use as a Subsonic & Minecraft server and I originally had everything setup as a nice well behaved homegroup with my current desktop and laptop so I could easily move files back and forth between the server and my main desktop. However, my new roomate is a Mac user and to give him direct access to the server to be able to easily put his music on to the subsonic server or access the other media that's not there I had to switch from a homegroup to a workgroup. I made him an account and he has no problem accessing the folders I've shared.

On my Win 8 desktop, when I go to folders on the server I can see them but it says I don't have permission, I made an account in the workgroup with the same computer name as mine and it never prompts me for a login. I've tried just trying to run a homegroup and workgroup at the sametime and sharing it that way. No dice.

Network discovery is on
Printer and File Sharing is on
HomeGroup connections is set to Use User Accounts and passwords

This is true for both the Win 8 computer and the Win 7 computer.

Thoughts on what to try?

Is there an easier way to give both my Win 8 desktop and my roomate's Mac access to the shared folders on the Win 7 desktop?

It may help to first remove both machines from the old Homegroup, it sounds like one of them was still part of the original Homegroup.

I'm not so sure about the Mac working along side a Homegroup however, in order to share Library's to machines which are in the same local Workgroup but not included in the Homegroup, you need to click on a Library then choose "Specific People" then open the drop down list and choose "Everyone" and select read/write access as required.

This will share Library's outside the Homegroup, local users in the Workgroup will not have access to your Library's unless you do this.

This is different from the other Homegroup users who would typically have access to all shared Library's on all other Homegroup machines.