Crowley's Boat Yard in Chicago where the OP launched from I beleive is a very reputable place, Much like Zanheisers, Harbor Haven, Port Annapolis or Hartage in our area. They have more business than they can handle. I would supervise their work carefully.
This problem you have I would use a professional as was mentioned before.
Crowley's is very busy. Staying on top of them is key, as you said Dave. I called three days in a row before getting a hold of the glass guy but I'd rather think that he's out there completing work orders on the boats that are holding us up than chatting with customers, so I'm not too upset. I would only consider having a pro do this and with as much work as they have going on there I'm sure there is no way they are in the habit of giving precious lift time to some DIYer who will take three times as long to do the job.
The OP did launch from Crowley's and the glass guy I spoke with today has been there 27 years, so he's handled anything that was done on the boat. He said he knows he has never touched this keel, apparently he's sure he'd remember it. It's never been rebedded, he's the only one who would have done it. While he was also perplexed by the stack of washers on the keel bolt he wasn't convinced it indicated a repair. As I said, he claims he would have been the one to do it and wasn't certain it wasn't done by C&C.
Unfortunately, I'll also have to pay to take the mast down so they can get to that keel bolt, but hopefully they help me out on price for that.
He said there is a chance there is not also hull damage under the keel, despite the odd manifestation of the leak, so fingers crossed on that.
They are going to do what they can to get us back in by next weekend, but it sounded like that would take a miracle. I know they have some bigger, much more expensive boats that need work done before the Mac, which we aren't doing this year.
I'm devastated to be out of the water, I was on it almost daily before this. I'm glad we are getting it taken care off though, and if this guy has spent 27 years at a yard with 1,000 boats I'd have to guess he's seen just about everything. Also, considering how much more expense Crowley's is than the other half dozen or so yards in Chicago he must be darn good at what he does. I have no worry the work won't be done correctly.