Over on the SP Ladder we created a Mentor Program, and it is offered to new Boots when they sign up. Essentially the Custodian has a list of veteran players who have volunteered to play a new Boot and not only help him, but explain in detail on each turn what works in what situations and why, etc The Boot in encouraged to ask questions, and the Mentor is obligated to answer them, no hiding behind the "I don't want to give away my plans" dodge. Both the Boot and the Mentor receive ladder bonus points, and you can only play 3 Mentor games (to avoid people padding their scores).
Having said that, not many new Boots take advantage of the offer. It has been my observation that only about 20% of the people who sign up for a ladder ever actually play a game, and only 20% of those that play a game play more than 1. Why that is I don't know (and those numbers are impressions not scientific data collection). I "suspect" that as others have said, many people are just shy or sign up on a whim when they find the website and never come back. A good percentage of those that sign up are humbled by the vast differences between playing the AI and playing PBEM. In the long run, so few Boots go on to become hard core regulars at this (or any other club) that when playing a Boot it is adviseable to be gentle. If not on the battlefields, then in the emails. The ones brave enough to get a game started can probably stomach the losing, but if they're gloated at they'll probably take off mid-game or right after.
So, my long winded rambling answer to Pete's original question is, IMHO you're a newbie basher if you're playing a Boot and are not only beating him, but you're also gloating about it like you've just beaten someone like Randy for the first time in 20 tries. Other than that, you're probably not bashing, unless you play the same Boot repeatedly. No harm in teaching a hard lesson to a Boot, but you don't have to teach him 10 games in a row either
Paul