Re: NEW Sailor, needing boat advice for fam
I'm with Shnool, the first thing to try to figure out are your priorities and your intended use case. Will you be trailering or keeping her at a dock? If trailering, what kind of tow vehicle do you have? The Mac is going to be much lighter than the O'Day, which makes it much easier to transport. But trailering can be a pain, especially with kids (I have 2 boys, ages 7 and 5). It takes time (30-90 minutes, depending on the boat and how much you're able to "automate" and are willing to invest in the automation) to rig the boat before you launch, and about the same time to break the boat down again before you can leave. Are your kids patient enough to handle that time?
Assuming your car/truck/SUV/pick-up/etc. can handle a boat and trailer's weight (add on an extra 500-1000 lbs for engine, gear, supplies, etc.), and assuming you're OK with the time element of setting up the boat (or if you're going to keep her at a slip or rigged on the trailer at the marina), then you can move on to the configuration of the boat itself, and how you'll use it on a daily basis. Will you be overnighting, or just daysailing? If you're overnighting, you'll need a boat that has, or can be made to have, sleeping capacity for your family. In some cases, you can cut sheets of plywood to span the port and starboard settees and, with the addition of an inflatable mattress, you can get a nearly queen-size bed in there, which is pretty nice, especially if your kids will fit in the other available bunks. If you're planning on overnighting on the boat, I'd prioritize the size of the cabin over the size of the cockpit because a good bit of your time aboard will be spent while the boat is at rest.
By contrast, if you're going to primarily daysail, I'd prioritize the size of the cockpit, because you will primarily be using the boat while she's in motion. When you're aboard to inspect the boats, sit down in the cockpit with the tiller in your hand. Make sure you are far enough forward that you can comfortably move the tiller. Now position your family so you can move the tiller from side to side without hitting anyone. Do they all fit comfortably? Do you have enough room for the kids to grow some before they aren't comfortable?
Next comes the safety factor. Are there lifelines and a stern rail? Are they an appropriate height/shape to allow your family to be safe? How is the visibility when you're sitting at the helm? Can your kids help steer and actually see forward while doing it (mine couldn't on our Catalina 25).
When our C25 was totaled, the issues above weighed heavily in our selection process for our "next" boat. In the end, we realized that we wanted a boat with a wheel (can't hit your kids in the head with it, unlike a tiller...and yes, I'm embarrassed to admit I've done that), and with a cockpit that was big enough for all 4 of us plus at least one or two more guests (our parents come along several times a year). It is VERY tough to find a wheel-steered boat in the 22-27' range. Some of the newer Hunters have 'em, as do some Mac's, and some C27's have them too, but many of them were out of our price range. A Hunter 28.5 is a nice boat that fit our needs, as would a Catalina 30. If the Mac has a wheel, as much as the wheel reduces your ability to "feel" the water and slows your reaction time (it's much faster to shove a tiller than to turn a wheel), you may find that it's ultimately more enjoyable than the O'Day with a tiller.
In the end, only you can decide what your priorities are, but hopefully the above will give you some things to think about. Ultimately, go for the boat that is in the best structural shape that comes closest to meeting your needs/wants.
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