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I discussed this with my father-in-law last night since I have a sort-of similar situation going on with a disolved partnership that I was a part of (long story). When we were talking about hypotheticals, I remembered your post. He said to talk to the IRS but to document every discussion you have. Your best guess should be OK, especially if you don't have the required documentation from the employer/contractor. The burden is on the contractor, not you, to produce the right forms, and by estimating on the high end, you should be ok. Note: none of this should trigger an audit unless you're going from a very high tax bracket down to next to nothing. Any sort of audit would pretty much be random, and if it turns out that you've overpaid, then you could end up getting a refund.
Good luck!
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