The boats we've been looking at are all relatively old pocket-cruisers, for example the Alberg 22, C&C 24, Catalina 27,, Georgian 23, Hinterhoeller Shark etc... Can anyone offer some advice on this? From the research I've been doing no one make or model jumps out as being perfect. Any advice (or info on a boat in the Canadian great lakes region) would be really great!
Of these, some comments - Alberg 22 - very solid, very tiny
C&C 24 - decent choice
Catalina 27 - lots of space, ok quality,lots to choose from
Georgian 23 - crudely but solidly built - lots of space for size including standing head room; not many around so you might find one that is cheap; needs a good wind
Shark - good boats, still raced widely so that tends to keep the demand and price up
For your purpose I would tend to look at the Catalina or the Georgian. BUT, be aware that selling any boat will be very hard in this market, so be prepared to be stuck. Georgian might be hard to sell because it is not well known - but that should help you get a good price.
I absolutely would not limit myself to the Canadian side of the lakes. You are almost certain to get a better deal in the US where the market is very depressed. Boat prices in Canada have fallen but not as much as they will. Bringing a boat into Canada is not hard and the subject has been covered in other discussions here. Note that the country of origin and the age of the boat has an impact on the tax payable on import. You could even get a boat in areas like Long Island Sound or New Jersey. Taking a boat back to Lake Ontario on the Hudson and Erie Canal is not hard and an enjoyable trip. You would need a reliable motor for sure.