One of the first things I look at is the pip count. If I'm behind
then I'm less inclined to step up. What am I trying to do, convert
to a losing race?
The next thing I look at is the opponent's attacking potential. Here,
the opponent has a better board and an anchor, so is happy to attack.
That also makes me not want to step up.
Of course, in any position, there's always the question, what else are
you going to play? If a move looks bad but everything else looks worse,
then one is going to choose the least evil option. My inclination is
to make the 5pt here. It does leave a direct shot but it gives us the
best upside if we're missed.