It depends on the situation. There can't be an outright answer to this. It depends also on the personality of the person, and sometimes it also depends on the nationality of the person. From my experience of Westerners I would probably lean more to the first one, from wisdom to reach a state of calm. Because for many Westerners, their type of personality doesn't lend itself so easily to getting calm first and then developing the wisdom side. So it often depends on the personality, the nationality and the situation. But I can't say a hard and fast rule to that, because sometimes in the course of day to day existence it may be that we need to get a little bit more calm before we develop the wisdom side. But on the whole, I would probably say that for Westerners it's more skillful to develop the wisdom to reach a state of calm.
Now one of the reasons is that because of the conditioning of western society, in which there are a lot of foundations missing of Right View and Right Intention. In Thai society, there's a lot of conditioning of, or at least talking about it, even if people don't practice it, for developing some Right View and some unselfish emotions. So that when the Thais then come to the intensive practice they have quite a different level of foundations. They also have a lot of more confidence in the Buddha, Dhamma and the Sangha, so they don't have so much doubt arising. Therefore on the whole some of these people can get calm fairly easily and from that situation they can then be much more encouraged by their Thai teachers to develop more wisdom, although many Thai people tend to get a bit stuck on calm as well. But at least there are many teachers who will encourage people not to get stuck on this.
For Westerners we have a lot of conditioning developing the individual and there is not much encouragement for developing Right View about the Four Noble Truths, Death, Impermanence and also the unselfish emotions. Because of such conditioning, frequently we're encouraged by society to develop selfish emotions. So with these wrong views, if a Westerner is encouraged to develop a lot of calm they may go into the calm with all this wrong view and wrong intentions and then they get attached to it. They may then not come out of these wrong views and not be able to practice the other factors of the Noble Eightfold Path in their normal life. And because they get attached to the calming side of the meditation, then they have resistance arising towards developing the wisdom side or the unselfish emotions. Then this often means a resistance to open to the unpleasant in themselves, developing the understanding of the Four Noble Truths and taking responsibility. So this is often difficult if a person has had experiences of calm and pleasant feeling in their meditation, developing the wisdom side is perhaps seen as too much work or too difficult.
For Westerners we prefer them to develop a necessary foundation, and see calm as a useful tool rather than an aim in itself. With more wisdom and Right View then if these people do get some calm they can see it as a part of a balanced practice rather than just the aim of the practice. And as far as getting calm, you can get calm from wisdom by changing the view. Sometimes this is very powerful and can also increase the factor of wisdom at the same time. So these are very useful ways of reaching calm.
In the beginning before I practiced a lot of formal reflection meditation, I had done it a lot in my daily life. I had some doubt about this, whether we could get very calm from wisdom. However, after we met teachers who encouraged using wisdom type practices, I saw that actually you can get very calm from developing these wisdom practices.
Now, as far as whether it is appropriate to the moment: sometimes when the mind is particularly agitated, it may not be appropriate to reflect, trying to get calm from the wisdom side. Because the mind is just too agitated, there is too much restlessness. At these times it's often more appropriate to do some type of calming meditations. For example, the walking meditation can be directed either to calm or insight, depending on how you're viewing the meditation. If you get a lot of agitation in the mind it's more appropriate at that time if you can't seem to break through this agitation to focus more on the calming side of the meditation and just walk more directed towards calm. In the same way the breathing can also be directed more towards calm or insight. So when there's a lot of agitation and a need for tranquility, one can direct the meditation more towards calm, watching the breathing more towards calming the mind rather than seeing the changes in the breathing. So it also depends what is appropriate in the moment.