I'd skip the windlass, or at the very least closely read the manual for the windlass they supply. If you actually followed the instructions in the manual, you'd find that it should only be used for the final vertical haul-up of the anchor. The maintenance schedule on it should be reviewed before purchase, too.
You decide whether the ultra-leather is a decent upgrade over cloth. We bought our's off the lot and it has the ultraleather, but it hasn't really made our lives any better...cloth'd be fine.
I would seriously consider not having Catalina supply the dodger and/or bimini. They are of medium quality, and you could probably do better locally. Also, the hardware is put on by the dodger people, not Catalina, and it's not properly bedded. We had hairline cracks as a result. Also, I'm 5'11" and the top of the dodger is right in my line of site when I stand at the wheel. A couple inches shorter would have been real nice.
The folding wheel is nice, but I don't fold it very often. It's not that hard to simply remove the wheel if you plan to entertain in the cockpit. The leather wrap's nice, though.
If you get the furling mainsail, beware. We had to have the vertical battens removed (and leach of the sail re-sewn) because they jammed in the mast. It's no fun to have the sail half out and JAMMED. Either find out from actual owners whether the current batten system actually works or don't get them.
Regarding headsail: we have the 150. The 309's a boat that relies on it's headsail a lot. I'm happy daysailing on just the headsail often. Sailing on just the main doesn't seem to work so well (even when the batten's were in it...no real difference). Still, it might have been nice to get the 135 and some sort of assymetrical for downwind and light air. I say that because the 150 is often more than we need, and you can only furl it so much without changing the shape of the sail. And the 150's more to deal with every time you tack as compared to a 135. I don't have the final solution, but you're right to be thinking hard about this.
I don't know if they're stock or not, but the curtains are not the greatest. The pleated design looks nice inside and out, but they're difficult to roll up. Try 'em.
Our boat came with the little cocktail table. We used it at first, but now it's stored at home because the stock (big) table is so handy. Switching back and forth is kind of a pain because the big table stores in the aft cabin...gotta be wrestled out.
Our cradle doesn't have screw jacks in it. There are pins instead, so you can't micro adjust the pads to the hull. That's stupid, as it means your yard will have to do extra shimming under the keel and maybe at the individual pads. And hopefully do it right. My ex-yard did it wrong and damaged my boat. This would be something to try and negotiate. I'm going to slide some pipe into each of my uprights to take up some of the slack and then slip screw jacks into the pipes, but that'll cost me about $400.00 or so.
I don't know what they charge for a stereo system. Our boat didn't come with one, but it's prewired for the speakers. Because it's wired, it would certainly an easy job to add your own if you're fussy about the components...be interesting to see the cost difference if you're in
terested in a sound system.
We never use the optional folding door for the forward cabin.
