Update: I resolved the Java issue. For whatever reason when I downloaded the normal Java installer, Windows wouldn't recognize it. I opted for the offline version, which was a much larger file, but it ran and installed successfully.
After doing this I realized that there were many programs on this thing, though not often used, that are very much out-of-date. I went through uninstalling those not used or unimportant, while updating all those that I deemed keepers. Then I went and ran a check at dslreports.com (which now works perfectly after the Java update). I found that my upload was MUCH faster than my download speed - 200K up & about 55K down. This led me to tweak my RWIN value and also set a basic MTU allowance. I used the DRTCP program also provided on the site to make changes.
After rebooting and rechecking, my download speed is consistently running between 350-400K and upload speed is still holding around 180-200K. So, looks like after a few nights of cleanup and tweak I've finally gotten somewhere. Thanks for all the help and suggestions you guys!
See you all on the server SOON..