I recall having problems with authentication in older versions of wine (1.4.x is quite old), but at the moment it no longer seems to be a problem. I would get the WSACancelAsyncRequest stub error in the terminal which would prevent DNS lookups from working. That function call appears to still be a stub in the latest git snapshot of wine, so it seems that either something else changed in wine that no longer requires that function to be called or something in blockland changed that made that no longer necessary.
Anyway, I'd try current stable (1.6.2) and if not that, latest unstable (1.7.13). I use 1.7.12 and have no issues hosting a dedicated server related to wine.
However, I too cannot seem to control the console through stdin, so that sucks.