Well, considering that you asked this to be resolved by a group of guys that over the past couple of years have made themselves into experts at finding secret places to find internet access, I am pretty surprised that people haven't been jumping on top of you. Then again, maybe most of us don't want to give up our secrets.
Seriously though, I do agree with the opinion first stated by Me3. This will only add a new dimension of possible harm. However, if in actuality it can't possibly get any worse I would suggest that he find a Rav or Sponsor, and meet with them on a consistent basis, in which he can use the meeting time to post his thoughts on GYE in addition to his spending time speaking with this Sponsor or Rav. This way it will be supervised, and the possibility of learning all the very wonderful nuances of traveling the internet will be avoided. If possible, this Rav or Sponsor can even spend time helping him to interpret something that someone else posted that may be of great assistance to him. Just an idea.