Some philosophers are bold; they defend strong positions with few hedges or caveats. Others are cautious; they defend weak positions with many hedges and caveats. Which of these two approaches, bold or cautious, is better?
I can't offer a full analysis of what it is for one philosopher to be more bold (or less cautious) than another. But I can suggest one sufficient condition: if the central thesis defended by philosopher X is logically stronger than that defended by philosopher Y, then X is more bold (less cautious) than Y. For example, if X's position is P, and Y's position is P or Q, then X is more bold.
Now suppose that two groups of four philosophers are asked to take up and defend positions with respect to two propositions, P and Q. One group is bold. The four philosophers in this group adopt the following four positions:
B1. P and ~Q
B2. ~P and Q
B3. P and Q
B4. ~P and ~Q
The other group is cautious. The four philosophers in this group adopt the following four positions:
C1. P or ~Q
C2. ~P or Q
C3. P or Q
C4. ~P or ~Q
Notice, each philosopher in the first group is more bold than at least three in the second group (e.g. the philosopher who defends B1 is more bold than those who defend C1, C3, and C4).
Which group, if either, has a better approach? Which group would you prefer to be in?
If you want to maximise your chances of defending a true position, then the cautious approach is for you. Three cautious philosophers defend true positions, whereas only one bold philosopher defends a true position.
On the other hand, if it's more important to you to know what the truth is, regardless of whether it's a position that you personally defend, then, arguably, the bold approach is for you. There is reason to think that the bold philosophers, working together, are more likely to discover the truth than the cautious.
Suppose we ask both groups of philosophers whether P is true or false. The bold philosophers will divide into two opposing camps, two saying "True" and two "False", whereas the cautious philosophers will all sit on the fence, all of them saying "Maybe true, maybe false". While we we can therefore expect lively debate in the bold group, we can't expect any debate in the cautious group. If philosophical debate is conducive to discovering the truth, then the bold group is more likely to discover the truth.
(Incidentally, I'm unsure of the precise relation between bold-vs-cautious philosophy and badass-vs-wussy philosophy.)