seeking first boat

[CalebD]

Jamie,
I'm not sure who doesn't like the long overhangs and lines of something like a Shields or ____ (fill in the blank). Boats like this I find to be breath taking.
You have been given some great advice by rgscpat and mstern above.
What is important is to know before hand how much work YOU will be required to do to make your CREW happy. I am glad to hear that you want to take your family sailing with you as this can be a great time together. It can also go the other way with unforeseen circumstances.
I would suggest you try to rent or charter a boat once you have some kind of certification (which does not have to be USCG). This will give you some insight into what some of the more 'modern' (chlorox bottle) style boats have to offer in terms of amenities and systems. It will also give you an idea as to what you want in your own boat or do not want.
Another option is to try to do some crewing on race nights at a local sailing club/yacht club or marina. The more you get to see of other peoples boats (OPB's) the more you can figure out what it is you really need and want versus what you think you need and want.
Older boats may be cheaper to purchase but usually require more money for upgrades and maintenance that may not be visible to the naked eye.
Get on as many OPB's as you can as this will help you figure out what you can live with.
All boats are compromises.
Mine is from 1967 but is a classic plastic sailboat.
The MacGregor 26 S would fit you and your crew but is more of a 'clorox bottle' boat as rgscpat mentioned. I've sailed this boat and it sails pretty well and has room down below for sleeping more then my Tartan 27'. My boat is more heavily built and ready for some rough weather while the M 26 S would not be my choice in a storm.
Good luck in your search.

[daydreamer92]

A suggestion while window-shopping:

If you live in an area that has a lot of marinas, take a walk along the waterfront with your camera. Snap pics of what you like. Visit boatyards and see what's still sitting there. You might find what you like is for sale within whatever budget you've set for your first boat and not in too bad of shape. Read SDs "self survey" post -- that'll help you weed out the "big project" boats vs. "can get it ready to go soon" boats. Check out craigslist and ebay and the other usual suspects and look at photos to make a list.

[erevllocin]

I have finally returned from Quebec and Nova Scotia. I am sorry to have taken so long to respond to so many great responses and thought provoking replies.

I am getting closer to what I want married with my expectations. However, I have only seen these boats on paper/internet. I need/want to step on board or better yet, sail. I am going to the Annapolis show in a couple of weeks.

Based on all that you have provided, I believe I am leaning towards a Tartan 27/30 or an ODay of similar size. I am, of course, still open to all kinds of alternative push and pull.

I have sold my F550 which was obviously a big mistake, and only have a truck whose towing capacity is 5K. That won't handle a 27-30' foot boat, but perhaps you guys can suggest something with a water ballast to reduce the weight.

Getting another truck or hiring haulage is not a big deal, however, 8'6" is the demarcation for hassles permitting. I am also convinced I will upgrade in one or two seasons.

I look forward to your input.

Jamie