I wouldn't worry about Windows saying something is corrupt. It says that whenever you connect a drive that wasn't formatted in Windows. I get that all the time with flash drives I format in Linux, and when I let Windows "scan and repair" the drive it always says no errors were found. That's just Windows being stupid.
As for your issue, that is odd. The first thing I would suspect is your HDMI>VGA adapter, because I have found those to be troublesome in the past.
Are you sure the Pi is not booting? Have you tried to SSH into it when you're getting no video?
Try adding hdmi_force_hotplug=1 to your config.txt file, and maybe config_hdmi_boost=7 as well.
My mind is like a browser. 27 tabs are open, 9 aren't responding,
lots of pop-ups...and where is that annoying music coming from?