There have been countless pieces written on this topic but frankly I never read them until I got a new 24” monitor that had a HDMI input. I was not happy with the HDMI from my PC to my 40” so I hadn’t planned on bothering with the HDMI to DVI on my 24” monitor until I saw an Amazon HDMI to DVI cable at a reasonable price ($7.49). What the heck, I bought it and tried it out.
I saw no difference between VGA and the DVI/HDMI. I found this curious so I googled VGA vs. DVI/HDMI and most of the posts I found were several years old. I did find one post that was more recent and made sense. The bottom line as I could see was that unless you have specific video needs there isn’t a whole hill of beans difference. VGA is analog and DVI/HDMI is digital so theoretically digital should be better. However the majority of users are not involved in situations that stress either choice. 
BTW there are several HDMI connectors so once again a picture is worth a thousand words. I own 5 HDMI cables and of course none of them were HDMI to DVI. The picture at Amazon made the cable selection very easy.
So if you have VGA and are happy with the visual aspect you probably don’t need to upgrade. If you are running some serious video components and want to receive your audio signal digitally (DVI/HDMI carry audio and video digitally) then DVI/HDMI is a better choice.
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