What affordable "type" is best for longterm cruising?
Jared - I''m also Canadian and will be heading south this year. There are boats you can buy for under $10k Canadian that are suitable for living aboard and cruising the islands. You have to be prepared to rough it a bit tho.
Examples: any Pearson Triton in reasonable shape will go around the world, price range from about$7500 cdn to $20k. My old boat, Challenger 24, sisterships have done Toronto to Honduras, I''m selling it for $7800. There''s an Alberg 30 for under $15k on sale now too. Check around, read lots, such as Vigors Twenty Small Sailboats to Take you Anywhere.
But forget about cruising in a houseboat - unless of course you''re looking to kill yourself. As for a cat, you won''t find anything worthwhile in the price range you''re thinking of so forget it.
Good luck, contact me directly if you want more help or info.