Why not use the 90 degree Dew Shield + for the Telrad, only a few bucks and handy so you don't have to bend down. Bintel sell them...
http://www.bintel.com.au/Accessories...oductview.aspx
Or...
Going by your original idea, you would probably be better off using a low light camera such as a watec902h or 902h2. these are low light cameras they use for meteor observations. I doubt the webcam would have the sensitivity for you. You could feed the video into a program like Sharpcap or even PHD and superimpose the reticule onto it.
Pointing the camera at the Telrad to use it's circles wouldn't work either unless the lens you were using is all-in-focus. If focused on the stars the Telrad would be out of focus, if focused on the telrad, you wouldn't see any stars.
I am no expert, but I do think using a low light sensitive camera such as the watecs would be the better solution. And there maybe other solutions also..