Damn, and just when I thought there was no greater piece of crap sailing to weather, than an Island Trader 38... (grin, bigtime) Just kidding, of course - I was favorably impressed by the sailing ability of the 45 I ran, considering the type of boat it is...
There is an Island Trader at the marina where I winter Argyle. Looking at that boat, I would guarantee I would smoke that guy (and I can't say that about many boats either).
They perform to windward about as well as an Island Packet, I've sailed with IP's and we're on par. I've heard they are a bit better than Westsails, but I've never sailed on or near one of those. Not to many heavy cruisers on Long Island Sound.
One of the things the Downeaster 38 is known for, is being underpowered... The standard factory install of a Faryman 24 Hp is woefully inadequate for that boat.
Absolutely! They originally came with either the 24 hp or a 36 hp as an option. I dropped in a Perkins 4-108 in Argyle (49 hp), which I've seen a lot of folks do. The original engines were also raw water cooled, so most of them are toast by now anyway. The 4-108 is about the biggest engine you can fit in there without doing some major cutting.
The Downeasters are also a bit underpowered sail wise as well. The 38 has a relatively short mast (43' 9") for a 20k lb. boat. You can always put up something big for off the wind, but upwind that short stick does you no favors.
I'd still smoke that Island Trader though!