When running Parallels under Mac OS X 10.4.8 I am having a problem when trying to run TortoiseSVN on Windows XP under Parallels. When I add a directory to my SVN checkiout, which is located on a drive mapped to a checkout on my Mac HD, TortoiseSVN creates the .svn directory underneath it but then fails to create the .svn/lock file it requires. When I look at this directory in OS X I can see that it does not have execute permissions set. If I create a directory in a MSYS (minimalist Cygwin system) shell which starts with a . it has execute bits set in OS X. However, if I then "chmod 600" the directory in MSYS it loses those execute bits and further settings of 777 don't reinstate the execute bits.
I am using smartsvn and I just installed the windows client on my Parallels image (Windows XP SP2) and tried to run it from Windows on a shared folder from my OS X file system where I have been doing checkouts and updates with the Mac OS version of smartsvn. Like you report, something bad happens to .svn files after running the Windows client. The Mac OS X client starts reporting weird permissions errors. The only way I could recover was to do a fresh checkout of my module from subversion using the Mac OS X client. I have decided that folder sharing does not play nice with UNIX-style permissions in Parallels. I would like to have this work.
I've seen this problem in the past without using Parallels. I was using a normal Windows computer and trying to use TortoiseSVN on a network drive that was pointing to a folder on one of my Macs and getting the .svn/lock file problem. The problem is nothing to do with Parallels so no point asking them to provide a fix for it. Your best hope is to approach the TortoiseSVN developers.