Hey Kyle,
Nice matches! It looks like you found a bunch of "Front Strikes" where the striker part is on the open flap side. These are generally pre-1974 give or take a year or two. They changed to putting the striker on the back for safety reasons. They are obviously older and more collectable. Condition is always important in any collectable and this is no different. Collectors look to see if the striker has been used, if all the matches are there and obviously condition of the book. Some matchbooks can be Die-cut into fancy shapes or have special features that set them apart. Some people like to pull out the staples and remove the matches from the book for safety and so that the book lays flat for storage in a book or binder. I am not one of those people, but to each his own. Sometimes the matches themselves can be interesting. I have some where the matches themselves look like penguins or cowboys or something fun. These are great - something you miss if you removed them. Once upon a time people put alot of effort into matchbooks as they were good advertising. I'm not an expert, but I have a few from here and there. Someone else may have more to add. All that being said - I would say that the examples you have are most probably in the $2-$3 range. Maybe as low as $.50 or a buck at flea markets or as high as $4-$5 on ebay if you found an energetic new collector. Fun stuff though and nice history and graphics! Happy collecting!
Don