As usual, start with the individual cards, and then try to tie it in together at the end.
Five of Pentacles ~ I tend to see this as loss on the material level, not necessary money, but for example health, which is apparent by the boy that is walking along with his leg in plaster and using the crutches. Another interesting thing to note is that they are both walking past a church, the boy is looking up, and the woman is looking down to the ground, which is snow, thus indicating coldness, coldness in spirit, and possibly coldness towards other people and possibly towards themselves. It is interesting that the Pentacles are actually is depicted on the stained glass of the church. Thus indicating that perhaps that is where salvation can be, a place where you can go, which is like a sanctity, and the fact that you can talk to someone that is partial, ie a priest. This can be tied into the Hierophant verily easily, more on that later. So, in this case it could indicate that even though one is at loss, all is not lost, just need to open your eyes and notice what you have, and what is around you, and what can be offered to you, even if it is just advice.
Five of Swords ~ This is one card that I tend to have a little bit of difficulty with, but here goes *deep breath*. Well, I guess it could be seen that there is some sort of victory, but what sort of victory is it? And at what price? I mean the man in the front is smiling, almost smirking, looking at the other two people in the card. The other two have got their back turned to the card, and are further into the background. One is clearly upset, and is crying. It could be a sense of trickery, you know doing someone out of something so you would gain something, this sort of thing can be seen among a group of people, usually colleagues that work for the own company. Sort of spreading rumours, doing things to make themselves look good, while disgracing others, whether that is warranted or not, more than likely not warranted. But at the same time it could be the sense when you know it is time to leave certain things behind in your life, more than likely people, as you know that they are not doing you any favours. And really speaking, you would feel better for it, not having them in your life, but not straight away, it would cause you some pain to begin with, but eventually the pain will be eleviated, and you would see that it was for the best in the long run.
Five of Wands ~ This card is about struggles and conflicts, either intenally or externally. For instance, say, when you have negative thoughts, you can combat those negative thoughts by challenging them. On the other hand, externally, it could be either fighting or trying to build something but at cross purposes with someone else. Since Wands is about action, with little thought, perhaps that might indicate that one person might be doing one thing, and another person might be doing another thing, and it is supposed to be working towards the same thing, but it is not working since there is lack of thought or communication between the participating parties. It might signify that a change of tact is required for a successful outcome.
Five of Cups ~ I tend to think that this is a mourning period after the loss or the finish of something else. The beginning stages of, which you are unable to see the good things that you have gained from the experience, or whatever, all you can focus on the disappointment, the sadness, and what not that it has finished. Unable to see the benefits of such a thing ending. When the time comes, you would be able to notice the things that still remain, the things that are behind you, the things that you have gained, rather than the loss. When you do, you would be able to cross the bridge, so to speak, and treat it just as one of those things, it's just water under the bridge.
Overall, it speaks of loss, perhaps failure, but also about change and crossroads.
The Major Arcana is The Hierophant, as that is 5, and Temperance, as that is 14, which reduces down to 5. As sort of indicated in the Five of Pentacles, it might be just a simple case of going to a sanctuary, somewhere you can find solace in, where someone could counsel you and give advice etc, which relates to The Hierophant. Also, it might indicate that by you going through such experiences you would be able to advise others that are going through the same situation later down the track, as in "Been there, done that, wore the t-shirt." Temperance can be about finding peace after a difficult time, a time of torment, etc. It is about being patient, as well. Also it can be about balance, compromise and sharing, which can sort of go back to the Five of Wands, by doing all of that there would be no need for the struggle and conflict.
Just rambling, I have no idea if that helps!