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So choosing pictures...there are probably two main philosophies on this.
One is to select only a handful of the "best" photographs depicting an event. The second is to use the photos you want to preserve of an event - sometimes many more than less.
I tend to take the second approach. When I get ready to scrap an event or part of an event, I pull the photos relating to that event from my "holding" books. I'll sort them by "theme". For instance, right now I'm working on a section of my DD's Girl Scout book. She served as an Honor Scout last summer so I have pictures relating to training, travel, their housing on Mackinac Island, flag ceremonies, her duty post, and a few more. These are the general categories I sorted them into. Sometimes it is a bit more chronological but that wasn't as relevant to me in this case.
Next step: I'll take the photos from one of the categories (I'll use training as an example) and lay them out on my work table. First thing I do is examine multiple shots of essentially the same thing, selecting the "best". Then I go through and begin arranging what I've kept to this point. Are there photos that maybe aren't so hot and really don't add anything? On the other hand are there photos that maybe aren't that great but add something.
At this point I've basically zeroed in on the photos I think I'm going to use. Now I start thinking about cropping and laying out. I hardly ever to less than a two page spread on something, and if the number of photos I have for one of these categories means 4,6,8 or however many pages that is fine! My goal is to preserve the memories.
In summary I weed out pictures that are essentially duplicates or really awful, but otherwise I'm more likely to use it than not.
As for software I have a little bit of lettering/journaling software but don't use it all that often.
Deb