Legally this is a new issue.However, the test case was IOD vs CORE and Ken Stubbs.
IOD
has registered several trademarks like yourself including .web and the.web.
Although
the case did not go against IOD, summary judgement was formed because the trademark
did not represent the nature of the business - only the type of business.
This
is as true for my.web as it is for the.web.
If you held the trademark to the word
"my" in the same way that IBM hold the trademark for the word "IBM" then you could
request my.web in the sunrise period just as they can request "IBM.web".
It seems
that you are in the same boat as the rest of us.
Your best bet is to try and register
your desirable domains with IOD, failing that you could wait and see in my.web is
still available after 60 days.
Remember that it should still be available as it
is not a trademark.
The question is - how confident are you that you'll get it??