Tom,
I've wintered at HHN for the past three boats. My last boat, a 1990 hunter 30g, had an iron keel, and needed some serious work. Osprey, who I assume you talked to, sand blasted and coated the keel in vinylester, and did an ok job. Ok meaning I wasn't thrilled, but I wasn't displeased either. I can't remember the cost, but I didn't regret doing it. I probably had it done in 2007-8, and it was still pretty good in 2015 when I sold the boat. I think my boat may have been one of the first they did in VE. I work in the composites industry, and had a long chat with them before agreeing to go VE vs epoxy. At the time they were using very high quality VE resins.
If you do have it done, I recommend
1. Wait until it gets warm before doing it. The resins are optimized to cure at room temp plus or minus a bit. If it is cold, they will take longer to cure, and moisture will collect on the uncared surface, not helping (here one of my chemical engineer colleagues could help out drawing hexagonal benzine rings on the whiteboard with bad things happening). You may want to consider launching with some bottom paint slapped on the rust, then hauling for two weeks when it is hot, and their workload is down.
2. Make sure there is a very clear understanding of how smooth you expect the keel to be. Mine had resin drips on it, even though I'd asked them to make sure it was smooth.
3. The keel has to stand on something while they work, so there will be overlapping areas. They missed a spot on mine because of that and it took two years to get it right. Inspect the boat frequently during the process.
I think they are a good enough outfit. That sounds like damning through faint praise, but there are a lot of seriously crappy companies out there - don't get me started on diesel mechanics! I've had them do 4 big (to me) jobs over three boats, and I would go back again, but I have learned to be very clear about my expectations, and check on the work.
By the way, I went through some trouble, including carrying a magnet around with me, to make sure my next boat had a lead keel.
PM me if you'd like to talk more. I'm hauled at HHN this winter also.
Paul