Typically the Board should put out some information as to the need and cost of the repairs as a matter of courtesy. For the amount they're asking for - most hold a meeting of some sort to provide information, but never to put it to a vote. Your bylaws will dictate what, if any, requirements of the special assessment there are.
Your bylaws will dictate what to do as for your roof leak. Some have a dispute mechanism. If the leak is a result of the actions of the roofer they need to go after him. Sounds like your complex has had water issues in the past - I'll bet that your condo has a ridiculously high deductible for water claims if that's the case, possibly no coverage at all. That'll be why they aren't / can't claim through insurance I suspect. If that's the case - don't count on the Board going after the roofer on your behalf - you'll probably have to go after them yourself.
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