I wouldn't recommend debugging the shell extension part if you're not 
already familiar with shell extensions in general.
While it is possible to do some debugging, getting everything set up for 
this takes a *lot* of time, and since you're dealing with the shell any 
mistake can basically break your system.

What I would recommend is enabling the debug outputs the tsvn shell 
extension has built in:
create a registry DWORD key under SOFTWARE\TortoiseSVN named 
DebugOutputString, and set the value to 1.
Then restart the shell (reboot is maybe the safest and fastest way to do 
that).
Then you can use dbgView from sysinternals (part of microsoft now) to see 
all the debug output of the tsvn shell extension. That might be enough to 
figure out the delay you have.

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