The O'Day27 was, like many another 27-footer half a century ago when every Tom, Dick and Harry suddenly had to be a seafaring man, specifically designed as a "starter" boat. As it came from the womb it was, like thee and me, utterly naked, so be not surprised that what you are looking at has an O/B
motor and no ground tackle. But since you are in La belle Province, you might like to compare the O'day with a Mirage27 which you will probably find superior in every respect.
Cruising, while on
passage, consists of long stretches of utter boredom interspersed with brief interludes of aching anxiety. Folk from a seafaring tradition know that, and so did the designers and makers of these sorts of boats. Therefore these boats were designed to be
RACING boats as opposed to cruising boats.
Racing is where the jollies are, and these sorts of boats therefore tended to gather in flocks in order to facilitate racing. Small racing boats, as exemplified by the O'Day27 as it emerged from the womb, relate to cruising boats as sows' ears relate to silk purses.
Structurally, these boats are much of a muchness, and one will be as good as any other unless it's been abused.
The great merit of boats such as these is that the "entry fee" in minimal, say five boatbux, and for that, plus an annual
ownership expenditure of roughly another ten boatbux (if the boat is kept in a marina) you can learn the basics of boat handling and basic seamanship. You can also learn the racing rules if that is what you want, and there is absolutely nothing better than bashing around the buoys on a short course for teaching you sail trim and general situational awareness.
If you have not already seen this, do have a good look at the sail plan for the O'Day and see if you can determine just why it looks like that and what the implications are for cruising.
https://sailboatdata.com/sailboat/oday-27
While you are about it, consider that your maximum speed through the
water is going to be about 5 knots on a beam reach. What does that portend if you set out for, say, Trois Rivieres so you have to come home against the
current of the river?. I ask because in my 30 footer with an inboard
diesel, and a speed of 6 1/2 knots, there are times when I simply cannot make way over the ground going up the Fraser River.
Lots to think about. The O'Day will get you started, but bear in mind that the vast majority of the stuff you need to learn to be a cruising man is stuff you learn from
books. That is why we have Maritime Academies for professional seafarers. The boat is for giving you an opportunity to apply what you've learned from the
books. So given the time of year and your location, maybe you might consider postponing your
purchase till the spring, and using the
winter to do some serious reading.
All the best
TrentePieds