We started dealing with him in August, it took until the following April before he came through for us with our Flagstaff 29QBSS (Which by the way would probably fit your specs).
There's a lot to be said about sticking with a local dealer, especially in your case being on the island. If you don't by local you're going to have to eat about $400 in ferry charges (200 there, 200 back) every time you want any service done. As long as you're patient and you've got a good dealer, something will come your way.
A unit like yours would definitely fit the bill but there isn't any around here. I would love to stick with a local dealer but not when they see a giant $ sign walking around their lot.
I did cave and emailed the salesman explaining the justification for my offer, what else I can buy for the same or less etc.. I acknowledged the higher quality of his trailer and said it would be worth $4000 more than the Salem Cruise Lite I am looking at and upped my offer to $22,000 + Tax. That's $3000 more than my original offer (12% tax here).
If he can't make money on that and the financing then I have to walk. Bummer.
As for the ferry, I actually calculated it all out and it's actually $300 each way with a trailer of this length, lol. Dammit... I love the Island but sometimes it can create situations like this, where you are marooned.