One of the effective solutions is to construct a risk table, in which you list out:
- each option - the costs to perform the option - the likelihood of success of the option - the value of success via the option - the penalty of failure via the option - the cost to ameliorate failure of the option
And you never assign a 0 or infinite value to any of those factors; a range of .05 to .99 is usually appropriate.
For binary choices, this can sometimes be short-circuited by flipping a coin and asking yourself if this feels worse than the alternative.