Is the 17 likely to be in production for the forseeable future?
Only Hobie Cat knows for sure. As long as dealers keep buying/selling them, they'll keep making them.
What is the weight limit on the wings? I know that many pictures show two people sitting on the wings - is this practical even in rougher conditions?
The weight limit on the wings is 340#. The SE (with the boom) is a miserable boat with two people. There's just not enough room for two people to get under the boom at one time in a tack / jibe. That's why the 17 Sport doesn't have a boom.
If I ordered a boomlet, how easy is it to switch back and forth for when I have a passenger aboard?
Very easy - and cures the problem noted above.
Do you get to choose the tramp color for a new boat? Do the wing-covers come color matched to your choice of tramp?
Yes and Yes.
Can the boat be ordered with EPO2 rudders? Do they come pre-drilled for the boat or is this a 'Dealer/Owner installed' thing?
I believe the answer is yes on both counts.
Can you order a custom sail-color pattern? How much extra is this in general? What colors are available?
Yes, subject to the availability of sailcloth colors. You need to talk to the dealer to find out how much this costs. Many of the racers go with all-white sails because
they are hard to tell apart (can't tell who's over the line early, etc.)
Is the clear window the same material as the rest of the Mylar sail? Would it be feasable to have a totally clear sail?
No and no. The "Mylar" sail is actually a laminate of Mylar and Dacron. The window is a clear plastic.
What types of trailers are offered? Is this a dealer-dependant thing? How much would an average trailer for a 17 be?
You can get any variety of trailers - most of the "hard core" travellers like aluminum trailers (Trailex) because they're light and they last forever. They come in several configurations and have a bunch of options. They're about $2K depending on what you get on them.
Are boat prices set by the dealer or by Hobie? Should I 'shop around' several dealers?
Hobie has a "Suggested Retail Price", but the dealers set the real price. What you get quoted depends on what they have in stock and how long it's been in stock (new old stock will be less expensive than if you order a new one from the factory - and you'll get it a lot quicker).
Most of your questions can be answered by your dealer - Dan Carpenter at Hobie Cats Northwest in Seattle is a great guy to work with. He also happens to be a kick-ass 17 sailor. Tell him that Matt Bounds sent you (then again, he might charge you more for that!