Whether or not there are "stupid questions" is debatable. However, if there is something about a record, a resource, or an ancestor you do not understand, consider asking someone. They may be able to point out some nuance that you overlooked that even seasoned researchers don't always see. And if it turns out you are missing something obvious, you probably won't die of embarrassment. And if you do, well then you can ask your ancestors those questions personally.....