No, I've seen this problem before. I run EQ on linux, and I've seen terrible runs of 39/40 logins showing a blank server selection screen. It's a real problem.
I live in China, so I thought it was a connection problem, but I also tried this while traveling to the USA a couple of months ago, and -- same problem. It couldn't be a blocked port, otherwise it would either always work or never work. Then, I tried running this on a Windows install from China, and I can log in without ever seeing the blank login screen. I think that rules out a network problem, so it sounds more like some sort of race condition in Wine. I've gotten pretty good at the keyboard-only login-retry procedure
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At this point I'm not sure what causes it, or why the problem got worse with a more recent Wine version. There was a time long ago when the blank login screen under wine problem did exist but was much rarer than it is now. You mention that you see this issue only with a wireless connection. That's possible, and not something I can test as my laptop (vaio pro 11) doesn't have an ethernet port. It would be interesting if that's the issue; if I can get ahold of a USB-ethernet adapter I'll test this and update this thread with my results.