I've recently started playing backgammon and have been practicing in 5 point matches against GNU. What I've been doing to try and learn is to make my play, and then check what GNU suggests and see where my play fits in, but still stick with my original play.

What I've been thinking about is whether a beginner player like myself may be better off deviating from the optimal play (which I assume the percentages of winning are based on perfect play) in order to get into situations where I am less likely to make mistakes. Similar to say an inexperienced no limit holdem player using a Kill Phil type big pot or allin type strategy.

In the long run maybe it's best to learn how to play correctly......but pretend for instance I was playing for money. What would be the best way to limit my losses against a GNU at the expert level. I'm looking for a few examples of what I should be trying to do......should I try and break contact? Should I pass more?

Right now I have yet to beat it in a 5 point match and I've played many

The quick answer to your question is that you want to place heavy emphasis on moving your back checkers up to make an advanced anchor. Once you have an anchor, you can try to break contact with doubles and reach a pure racing position, where the chance you can make a serious error is minimal.

The real answer, of course, is that you want to improve your play and keep eliminating mistakes. The simple strategy above sounds very doable, but the dice often won't cooperate and you'll still find yourself in many complex positions that will be hard to play.