I wish I knew the exact answer to your question about Wineskin, but I use a VM on my Macbook pro.
I too encountered various weird blackout issues when I first started playing again 2 months ago on a newer Mac. In the end, I had to match both the resolution of my VM and the resolution of EQ in full screen mode to get it to not black out on me when I went full screen, and make sure the windowed mode resolution was displaying for the times I accidentally exited full screen. The main problem is that Macs don't seem to like anything that exceeds the size of the native Mac resolution in any direction on VMs.
Also, there are really 3 settings for screen resolution to modify. The first is the VM itself. The second is EQ's opening screens, as in the log in, server, and loading pages. The third is the game itself. IIRC, the eqclient modifies EQ's opening screens...
It'll take some trial and error in EQ to get the right resolution. Here are my settings if you want to try those out (not sure how Wineskin works):
VM (control panel): 1280x800 (full screen)
EQ (the opening screens): 1280x768 (cannot exceed the VM resolution)
EQ (full screen game): 1280x768 (cannot exceed the VM resolution)
EQ (windowed mode): 800x480 (I tend to run into issues if I make this too big...mostly just screen run-off, though)
I do like full screen since my laptop is a 13". Macs give you the ability to make multiple desktops, so I just full screen on one desktop and switch to another if I want to look up something.
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