Yes, the truth should be disclosed. But what happened when he was 17, may actually have a significant impact on what if anything can be done now. I highly advise that you speak to an experienced immigration attorney before you file anything as your husband may actually end up being worse off than he now is.
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All applications can be submitted at the same time, it usually helps the process go faster. You should attain counsel though to help you deal with the issues of his turn around.
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Before you spend thousands of dollarS on application fees, please spend a little money on consulting with an attorney. Your huaband's multiple illegal entries might subject him to the permanent bar that cannot be cured by grandfathering provisions of 245i even though he was a minor at the time. Whether he's subject to the bar depends on when this happened, how long he was in the us before he entered the first time, how long he was in the us between entry 1 and entry 2, and what happened when he was refused entry (deported or not).
The information offered is general in nature and not meant to be relied upon as legal advice. Please consult an attorney prior to making legal decisions. Visit us at www.tunitskylaw.com. Contact us at 713.335.5505 or email at email@example.com. Veronica Tunitsky offers in-person, as well as telephone and email consultations.
Attorney Tunitsky couldn't have said it better. You typically only get one "free out of jail card" so to speak, i,e, one illegal entry and a waiver for instance by being here out of status for one year or more. But more than 1 illegal entry and he may be out of luck. Consult competent immigration counsel since otherwise you'll loose all your application fees ($420, $1070 and $1000) and also he may end up in deportation proceedings.