I think if you have outgrown an Islander 24 you'll not find a Flicka or anything else close in size to your current boat much of a step up at least in usable space. The Contessa doesn't have standing headroom. The Haida is a good boat some of which have travelled far (John Guzzwell's son Jonathan sailed the Pacific in one that the next owner took from Victoria as far as Brazil), but the cabin version is the only version you can stand up in, not the flush deck version which is a better boat in my opinion. Norsea 27 is a good solid boat, many of which have travelled far - the centre cockpit is the most common and that's not to everybody's liking. Bristol 29 is a good boat as far as I know, but I don't think you'll find many on this coast. Have you thought of the Alberg 30 or the Vega 27. Both solid boats with more room than some of your choices. As far as engine most will have inboards and that I believe is the better choice in a boat over about 25-26 ft., but this Vega looks good and does have an outboard.
1974 Albin Vega Sail Boat For Sale - www.yachtworld.com
Budget is something you have not mentioned and whether you're willing to refit whatever you buy, as many of these older boats will need it after 30 or so years afloat.
Hope this helps.