After dealing with this problem for a while, it came to a head again recently and I went for the quick and dirty solution (Windows/DOS only):
:Beginning
@ECHO ON
svn cleanup %1
svn update %1
@ECHO OFF
IF ERRORLEVEL 1 GOTO Beginning
I named it angry-update.bat and stuck in my "scripts" folder (which is in my PATH). Shell integration would be nice, but I'm okay with changing my workflow for big updates.
Hopefully someone else finds this useful one day!