I can’t believe I didn’t notice this before.
EVE-O works fine when the previews are on my main monitor. I downloaded an old version to test that (v4.0 or so) and got very excited when I logged in and the preview was working! But, I moved the preview to my second monitor, and it was immediately black (in fact, I could hover the preview half between my main monitor and half my second monitor, was half was working half was black).
I tried the newest version and it is the same issue. I never noticed since after logging in the windows re positioned to my second monitor.
Would you have any idea what could cause this?
Edit: I can actually move the game client to my second monitor and the preview still works on the first monitor. The issue is the first monitor is significantly better than the second (the second main purpose being to hold the thumbnails, email window, etc)
Edit#2: It seems to all revolve around the primary monitor. I am able to set my second or third monitor as primary (so it has all desktop icons, etc), start the game on that monitor, and move the client to my best monitor. This keeps the thumbnails working on the secondary monitor, while the main monitor has the game. This is obviously very cumbersome to setup for a lot of accounts. I would love your feedback and still have ISK waiting 
Edit#3: I am becoming convinced that this is a display port issue. I have three monitors - one HDMI, one DP to HDMI, one DP. Connecting the DP monitor via HDMI seems to resolve the issue (I can start the client on my main PC, and move the thumbnail to the second PC with no issues). I do lose my third monitor, as my GPU cannot support multiple HDMI. It is very odd, as I am using the same monitors, cables, and GPU as my previous computer, which did not have any of these issues.