I'd like to know if it's legal to have a client software/web site to
take a screen shot of your desktop and send to them. Are there
restrictions to what the "fine print" can say about this?

For example this privacy statement:
http://www.multipoker.com/en/about_us/privacy.jsp

"Our software may perform any or all of the following functions in
order to detect the use of illicit automated programs and ensure that
we maintain a "cheat free" environment for all users: (1) scan your
list of active software applications while you are using the Service,
(2) scan your list of active processes while you are using the
service, (3) scan the files in your MultiPoker.com-related program
folders to ensure that only "non-hacked" versions of our software are
being used. If any of the foregoing processes reveals a suspect
application or process, our software may (1) scan the files associated
with the suspect application or process and compile a composite mesh
(i.e. a profile that characterizes the files associated with the
application or process) to be matched against profiles for known
illicit automated programs, and (2) capture a screenshot of your
desktop, and transmit these to MultiPoker.com for review."

That's like Ikea having a fine print that they have built in
webcameras in their furniture to document your life.

It is illegal for the program to scan files outside of its main
folder, that is, unless you waver that.  And most likely if you sign
up for that poker site, you accept all the regulations associated with
it - including scanning of your computer.  So in your scenario, it's
not illegal because you gave them the right to do so by signing up.

Regardless of your disclaimer i do believe that is illegal to scan
ones computer for such information. If it wasn't illegal all of these
big companies that lose money do to piracy would have the same set up.
I would set it up so they cracks and such wouldn't work. So what you
need to do is build defenses against these types of programs from
interacting with your software. Becuse regardless of a dislamier you
can be sued unless you specifically state what your are getting into.
For instance if someone d/l your software and you obtained some secure
info they and on there computer then you could be liable for invasion
of privacy. There are so many loop holes and if you are trying to
completly scan somones computer then you more than likley are opening
quite a few of them for whoevers computer you are rummiging threw.