If you have cake decorating and cookie decorating experience you will be fine. Don't be intimidated by making a gingerbread house. Although, you might want to practice making a small basic house with four walls and a roof before to test the waters and know what you are getting into before committing to do a big house for your school.
You can cut your windows free hand before baking. Then after it is baked you can stick gelatin sheets on the inside of the wall with a dot of royal icing in each corner (or all the way around) and you have instant windows. A lot of people make candy windows using a basic hard candy recipe. But that is a lot of work for a first timer. The other option is, as you say, to make windows out of sugarpaste (fondant) and then adhere them to the outside of the walls. You can design pretty curtains and window panes using royal icing on top of the fondant.
The best advice is to start small and have fun with it. If it starts to become stressful or seems like work and not fun, then you have bitten off more than you can chew the first time.
Best of luck to you.
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