http://bugs.winehq.org/show_bug.cgi?id=33795
--- Comment #6 from Dan Kegel dank@kegel.com 2013-06-30 08:22:28 CDT --- The key line in your log is
(0) : fatal error C9008: out of memory - malloc failed
This is starting to sound like bug 13335 or bug 24826 or bug 33858.
Which version of Skyrim? 1.3.10 (released Dec 2011) added support for 4GB RAM.
When on the true 64 bit system, does setting the LARGEADDRESSAWARE bit on Skyrim, or running wine with "setarch i386 -3 -L -B -R wine ...", help?