When it comes to Caldari, I think how Herko painted it makes a lot of sense. On the background, you have the virtues of loyalty, knowing your place and doing what you are expected to do as well as you can, respecting your superiors and ancestors, but instead of japanese style family ties you actually identify yourself with the megacorp structure. Their way of the winds seems to be compatible with the idea that you go where the natural forces take you and do what you must and generally glorify the self-sacrificing collectivist mentality.
In my opinion, we need to avoid getting too attached to the idea that the Caldari are self-sacrificing for the sake of collectivist ideals. Remember, the Caldari are hyper-capitalistic, meritocratic, and intensely competitive, traits which do not lend themselves to altruistic interpretations. Rather, the Caldari understand that grouping together usually increases your chances of personally doing better. Therefore, you and your colleagues compete so that you, together, can get to the top of your Division. Divisions compete within a Megacorp to advance their own vision for the company. Megacorps compete with each other for market share and to implement their vision for the future of the State. And the State competes with every other Empire.
The Caldari, as a people, built their civilization on a planet much harsher than Earth. This was a planet that killed the weak, and promoted the stronger leader, the stronger tribe, and the stronger nation. This explains much about the modern Caldari civilization: the strong social mores (social cohesion is important in dangerous conditions), the intensely competitive nature (resources are at a premium), the tendency to group (groups offer better chances for survival and specialization of labor), and xenophobia (the fewer resources there are, the more competition from outsiders to possess your land, livestock, etc).
Because of the national archetypes we have around us, it's easy to classify fictional civilizations as analogues of our own, but this is not the case. The Caldari are not, despite the names, either Asian or Finnish, and the Federation isn't the U.S. or E.U. So we need to be careful when reading a certain bit of PF to be sure to compare it with other PF. Defining the Caldari as a strictly self-sacrificial, collectivist culture ignores the PF defining them as often very individualistic, competitive, focused characters. And portraying them as strictly greedy and selfish in nature ignores the PF that shows them often having a good deal of patriotism and loyalty. And these are both, of course, gross generalities.
I personally see the Caldari approach best defined as "units of competition". You, personally, want to do well, better than everyone else around you, in fact. But outside of that immediate group, you also want your entire group to do better than other groups of similar nature (family, coworker groups, etc). And you want that group (company, Megacorp, The State, etc) to do better than others.
Because of this desire for competitive superiority, social attitudes and ideas which are (or appear to be) disruptive or even just non-useful tend to be considered a Bad Thing. This explains why gender equality seems to be the norm in the State, but homosexuality is not accepted - gender equality is an efficient use of labor, but homosexuals do not tend to reproduce, an important facet of survival for groups on a cold, hostile planet with high infant mortality. This can explain other things, as well: why do so many Caldari have tattoos in fiction pictures? Simple: tattoos are often a mark of identification with a certain group, and can serve to inform others of your loyalty to your common cause.
Of course, one should be wary of something that can explain everything. This is, of course, just my view.