All of these questions are hard to answer without being the person in the situation directly, especially with the "should I flirt " thing.

Thing is the best gauge for what to do in any given situation with another person especially one you are considering getting involved with romantically is to get to know them and discern the best course of action based on their behaviors, yours and a whole slew of things that only you and she will know.

Although there is no set standard for what is right or wrong when courting someone with the goal of a romantic connection at some point, going slow is almost always the best approach. People forget much of the time when they rush into romance that in a relationship the best basis is actually being friends first and letting the romance grow, because romance, passion and emotions come and go but the one thing that should be consistent is a close friendship. that's what will make the relationship last in the long run.

As for flirting again getting back to interpreting and understanding her actions, ask yourself if she seems open to flirting and if you're comfortable with it, some light flirting is a good test to see how she handles it, whether rejecting it or accepting it.

But overall focus on the more important things like friendship first. it doesn't have to be the end goal, but it's one that is fundamental.

Hope this helps.