The Eastern Eastern 20 2009 is a modified-V design and the Eastern Eastern 27 2010 is a deep-V design, so you're likely deciding between two noticeably different on-water experiences. Hull type shapes everything from ride quality and fuel burn to dock handling and resale trajectory.
Size is the most obvious dividing line here. The Eastern Eastern 27 2010 measures 26,3 feet overall (2010), giving it roughly 6,2 additional feet of deck space compared to the Eastern Eastern 20 2009 at 20,2 feet (2009). Weight tells a clearer story for trailering families: the Eastern Eastern 27 2010 tips the scales at 4 800 lbs - 3 300 lbs less than the Eastern Eastern 20 2009 at 1 500 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.
For family outings this is probably the sharpest distinction between the two. The Eastern Eastern 27 2010 is rated for 8 passengers, while the Eastern Eastern 20 2009 caps at 6. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Eastern Eastern 27 2010 could be the deciding factor.
Bottom line: Choose the Eastern Eastern 27 2010 if your priority is putting more people on the water - it handles 8 passengers and at 26,3 ft it has the deck room to back that rating up comfortably. The Eastern Eastern 20 2009 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 6 that costs less to run day-to-day.