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So after wanting to do this for years, I finally got this done!
Spent hours researching VGA boxes, VGA cables, upscalers and such. I finally settled on the retro-bit VGA cable, The Orei VGA to HDMI upscaler and now my Dreamcast is in glorious HD and looks beautiful and all for just over $50!
Stuff I purchased:
Retrobit VGA Cable for Dreamcast
OREI XD-600 VGA PC/Laptop to HDMI Video Converter -Upscaler Up to 720P/1080P Converter with Audio Jack
and for the audio for VGA I got This $5 adapter.
And it looks epic in glorious 720P! (Don't mind the messy cables still sorting things a bit)
So, how'd I do for $50? :D