Hi,
Well, I've finally started seriously looking for my first sailboat

I've found a couple not too far from me that I'd like to hear other's opinions about.
I guess I should give a bit of background information first though eh?
I live in Montreal, Quebec. I'm only 24 years old, so my budget is rather small. Then again my expectations aren't all that high either. While I don't have tons of sailing experience, I have sailed dingys quite a bit. I also am a REALLY fast learner and have read just about everything I can get my hands on online and offline, so like to think I'm not going into this blind. My cruising grounds if I stay local is a rather shallow lake (Lac St.Louis right up beside Montreal), or if I go a bit further which I am seriously thinking then Lake Champlain.
I'd like a boat that I could spend a lot of time on, so accommodations are a bit of a priority (decent head/shower) etc. I'm not looking for a floating condo by any means, and am single (

) so don't need anything huge, but if I'm going to spend a lot of time on the boat I might as well be at least a little comfortable no?
I'm not looking for something seaworthy enough to cross oceans in (yet

) but if one day I wanted to hop over to the Bahamas etc, it would be nice to know that I could without having to get another boat. (with the right weather window, and a lot more experience then I have now of course

)
So without further ado, here are the boats I'm looking at, and my thoughts. (also all 4 boats are with the same broker by coincidence

)
I can't post links directly so I had to mangle them a bit.
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1984 Catalina 27 - US$12,000.00
www dot boats dot com/listing/gallery.jsp?entityid=17996601
Pro's
- Brand name so should be easier to resell when the day comes and be easier to get parts for if needed
- Cheapest asking price of the 4 I'm looking at
- newish sails (Ad says 05/06)
Con's
- Smallest of the 4 I'm looking at
- Would really prefer an inboard motor
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1974 Grampian 30 - US$15,000.00
www dot boats dot com/listing/gallery.jsp?entityid=16670951
This boat is pretty much middle ground for me.
Pro's
-Inboard motor
-longer then the 27
Con's
-The motor is gas, I'd prefer diesel.
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1978 Beneteau First R/C 30 - US$17,500.00
www dot boats dot com/listing/boat_details.jsp?entityid=16998201
Pro's
-Looks really sharp, I like it's looks
-Production boat
-Inboard Diesel
Con's
-It's draft probably rules it out for my local lake.
-Most expensive of the ones I'm looking at.
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1991 Leeboard Gaff Ketch Custom built - US$14,900.00
www dot boats dot com/listing/boat_details.jsp?entityid=14417581
This last one has me really curious. I LOVE the looks of ketches/yawls, and the gaff rig looks nice at least. However I know next to nothing about both the Gaff rig and leeboards. Also the hull is listed as wood, however in the listing it says "strip planked western cedar, custom built and fiberglass epoxy clad." Does this mean it takes less maintainance then a fully wooden boat? I'm afraid that I'm not knowledgeable in construction techniques.
Pro's
- Super small draft with the board up (18 inches) and he says it's even beachable

-I love the "look" of the rig. Don't have any information on how it sails though
-listing says it has positive flotation.
-Comes with a trailer (not that I have anything that could pull it, though a couple of my friends do)
-inboard diesel
Con's
- I don't know anything about taking care of a wooden hull
- Not too sure about the leeboards. (I'm guessing that's what the thing hanging off the side of the hull is called)
- Built in 91, refits in 95 and 01, needs another refit?
- not the nicest looking hull in the world (to me anyways)
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So given those 4 boats, does anyone have any advice/opinions?
Thanks!!!