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You only need one Beginner's Box per group.
If you are only interested in Beginner's Box adventures, you don't want a subscription. The subscription is to the line of Pathfinder RPG books, which are a bit more complicated than Beginner's Box rules. There are some free, downloadable resources for Beginner's Box rules on this page, and you can buy extra adventures written for Beginner's Box rules here.
Later on, if your teens have gotten the hang of the Beginner's Box and want to move on to the more complicated, options-rich RPG line, some of Paizo's subscriptions might be interesting to them. The Adventure Path line provides two long-term adventures per year, at one book a month. The Module line provides a shorter adventure quarterly. The Campaign Setting and Player's Companion lines contain books with information and mechanical options for Golarion, the world Paizo's adventures are set in.
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The subscription that you are likely talking about is to new books that Paizo publishes each month. There are several different subscriptions, each to a different line of products. While I am personally subscribed to many of them, I wouldn't recommend that you get a subscription until you are more familiar with the individual product lines. It wouldn't do you much good to get a subscription to a line of products that you have no use for.
I don't think you want a subscription right now, but to answer your questions:
You pay the price of a book in a subscription whenever it ships. So, if you have a subscription to the Adventure Path line, you would be charged once a month; if you have a subscription to the Module line, you would be charged once per quarter. (I'll note that the schedule slips sometimes, so on occasion you might, for example, not get an AP volume in one month and get two the next month; in that case, you'd be charged for both when they ship.)
There is no contract, and you can cancel your subsciption at any time.
I'll also note that, apart from the Adventure Path line which gives you a 15% discount on most things you purchase from Paizo, the main benefit of most of the subscriptions is a free digital copy of the physical book. If you aren't interested in the PDFs, you can buy the books at Amazon and usually save some money.
If you're asking about compatibility with the Beginner's Box, it doesn't include miniatures but pawns like these, flat cardboard cutouts that fit in a holder to stand up on the board.
That said, you don't need minis or pawns at all, just some sort or markers or tokens to put on the map. I used to use different colors of dice, or you could use playing pieces from a board game: just as long as everyone knows which one represents what. I used pennies one time, when I had a whole mess of enemies.
There are subscriptions for the rules book like, the novel line, the adventure path line, the module line, ect. Each different product line has an associated subscription with a different price associated and those would bill monthly.
This is not exactly true. The AP line aims to deliver a monthly product so you would mostly be charged every month for that (barring schedule slippage), but the RPG Subscription, for example, only has three or four products a year, so you'd only be charged when they ship you a new product.
The main thing is that there isn't a charge just for the subscription. You're only paying for the products in the line whenever they come out. Most of the time (except for subscriptions that offer a discount), you could order the books separately for exactly the same price and same number of charges; you just wouldn't get the free downloadable digital copy.
People who subscribe to the product lines get products before they are released in stores so that's another perk of having a subscription.
This is not always true. Usually, subscribers at least get their PDFs before street date, but there have been occasions where, due to more than expected orders, subscribers have not even had their products ship (so as to release the free PDF) before the same products are available in store. Early access is an occasional perk, but Paizo does not make any guarantees about it.