MWrohde-
You want a sewing machine that has all metal gearing in it... since the plastic ones just don't have the punch to go through lots of sailcloth on a regular basis. There are quite a few Pfaff machines out there, and I'd highly recommend them. They have a lot of features that I'll never use, including the ability to monogram and embroider to some degree. However, they do go through five or six layers of denim, and more of Sunbrella, just fine.

You can probably pick one up on craigslist for less than $300, which is a good chunk less than the Sailrite Ultrafeed machines, and the Pfaff's will do zigzag and straight stitches.
__________________
Sailingdog
Telstar 28
New England
You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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