need boat advice...new to sailing!
Would suggest that in cold Canadian waters, a self-bailing cockpit is a good idea. If you like the P23, the thing to do is to make an offer of what you can afford for it. Even if the asking price is much higher, they might be under pressure to sell quickly, and (surprise!!) accept your offer. The worst they can say is no, and even then, you''re no worse off for having tried. The alternative is to keep looking.
With two daughters of my own, my advice is to get the largest possible boat you can afford, because you will need it desperately in five years or less. My personal slant is towards the J/fleet. Though J/24''s in your price range might be pretty tired, if there are some in your area, one of them might make sense. Their large cockpits and decks are ample for cruising and daysailing, and they''re fun to sail. Not much headroom or privacy, though, and if they''re not available where you are, the point''s moot.