When I was in touch with a SVCA representative several years ago they informed me that it was the SVCA's intention, at that time, to keep the development of the Trout Brook Preserve to the West side of Trout Brook. The East side would stay wild. I suppose there is also exploration that could be done into a trail system. As Wayne said- a very appropriate Eagle Scout project, Hornaday Award, or Gold Award project.
A technical issue with X/C ski trails is that many use a crude form of mechanized grooming- basically a roller which compacts the snow and puts 4 deep tracks into the snow for a 2-way trail. We might be better equipped to handle snowshoers than skiers, especially with the acreage at ToM. It's a short distance for skiing, but a decent length for some snowshoeing.
One of the "big ideas" in trail planning is to look at erosion issues and look at constructing trails which limit erosion problems. Another idea is timing- we can look at our service interval and plan trails which will, for the average visitor, consume about 75% of the time between trains. This gives visitors time for detraining, a short break, and being a bit early. Perhaps a nice idea to provide 2 loops- a short loop and a longer loop, share parts.
Here is a hiking time calculator that can help establish trail length/times
http://www.douglastwitchell.com/hikingcalculator.php.
Steve