Just an update for anyone who stumbles across this thread looking for a similar answer.
The Hammerhead Adapter came and seemed to work very nicely at higher resolutions, and while it still worked at lower, there seemed to but a lot of noise which increased the lower the resolution. I can't honestly say if it was an issue with my setup or the adapter, but from the reviews I've read and another thread on this forum it doesn't necessarily seem to be a consistent thing. If you need VGA -> HDMI I'd still say it's worth a shot, especially if you will work at higher resolutions. No input lag (or next to none) either.
With regards to my specific case, I was getting a bit disheartened when I reconnected the DVI -> HDMI adapter and all of a sudden it works perfectly! Not sure what happened, as I'm triple checked it was plugged in correctly.
Only issue is my monitor recognises resolutions like 320x200 as a 16:10 resolution so the top edge is ever so slightly cut off, but I don't think I consider it an issue. Not one worth worrying about.
Oh and I also learned Nvidia drivers on 98 definitely require trial and error. For example, 77.72 at low resolutions would repeat the image three times, making it unusable. On 81.98, if I changed to certain resolutions it wouldn't display and I couldn't even boot into Windows (well it'd load but I couldn' see anything on screen, just hear it).
All part of the fun though.