While in Southwest Harbor looking at boats in 2000,
I stayed at a B&B downtown.
Interestingly, I met a guy also staying there who used to be a part owner in the Hank Hinckley company, and who had owned one of their boats in the past. When I met him he had recently purchased a SW 42 or 43. I didn't get into any deep discussion with him about the differences, but he apparently liked something better about the HRH boats.
Hank Hinckley is still in business, albeit not selling the OC boats. He has a little website, although I don't know if you've seen it. HRH's website is much grander.
A couple of other observations. There are quite a few HRH sailboats for sale presently (as with most builders' products), and many of them have been on the market for a long time. Some of the SW 42/43 boats have been for sale for 2 years, maybe more. At the top end of the pricing is the '94 SW 43 now listed at $540K, but which was listed last year or perhaps earlier at, I think, $649K. It looks very nice, but the price differential between that one and the group of somewhat older boats (at roughly half the price) probably makes it a hard sell.
On the bottom of the pricing scale is the SW 42 in Stuart, FL. It also has been for sale a long time, and I think it too had a price reduction awhile ago. I thought about looking at that one when I was considering going up in size, and tried to stop by one day while I was in South Florida a few months ago, but the broker wasn't available when I called. From the photos I would say the exterior teak needs a lot of work and the boat appears to have lived a hard life. Compared to the New England boats, that one justly is considerably cheaper.
I suspect many asking prices are rather soft. You are probably wise to talk to an HRH broker about price trends and how long it takes to sell, and then go to someone not affiliated with the company to confirm the information. Companies that broker for their own products have a substantial interest in keeping prices high in the brokerage market as a sales tool for new boats. Good for used boat sellers and manufacturers, but not buyers.
When you talk to the HRH broker, you should also ask what layouts, interior woods, and other features make the boats easier to sell when that eventual day comes in the future. For example, I think the dark interior woods are not as popular nowadays as the lighter woods or laminates, and that's not something that can be economically changed once you buy. You might prefer darker yourself, but you should at least find out what the market in general likes best. Dinettes versus opposing settees are another issue.
All these boats are now 20-25 years old. The last bit of advice I'd give, only because I don't know if you've owned one of these expensive and complex beasts in the past (by that, I am referring to any larger sailboat), is to make sure you get a good detailed survey and that you are prepared to put in the large quantities of time and money that the wrong purchase can require.
In 2000 on the trip to Maine that I mentioned above I did buy a used sailboat which was 9 years old but had spent it's life in the south. The closing price on that boat was a trifle less than some of the OCs now for sale.
Here was my error: I completely underestimated what it costs to own and update a modern sailboat, and promptly spent about 50% of the original purchase price during my first two years of ownership. Financially, you are better off buying a boat that has fairly recently been renovated or upgraded than doing it yourself or paying to have it done as the market doesn't reflect accurately what it costs to upgrade or replace.
Good hunting.