With your goals, spending money
on a better boat in the first place will end up saving you money (and maybe more) in the long run.
We had nice weather
on a Marblehead-Halifax Race
once, roaring down 15' swells at better than 12 knots on a 42' sloop
. More breeze or a different tide might have made them breaking waves. Not something you'd want to deal with in a 28' boat 100 miles off shore en route
to Sable Island. Figuring a generous hull speed
of 6.5 knots for a Morgan
28, it would take about 15 hours to sail the 100+ miles from New Harbor to Sable Island. Perhaps possible if you could stay on a broad reach all the way, and the wind
didn't die, change direction, or mood. Any of those things happening could ruin your adventure, turning it harrowing, worrisome, or dangerous, depending on the weather
and your skills. As tkeith suggests, seaworthiness depends a lot on the sailor knowing what his or her boat can handle, and how to handle it. A bigger, better boat would make knowing how to handle such a trip easier. If I made such a trip on my boat, my liferaft
would be on board.