The Eastern 27 2008 is a modified-V design and the Eastern 27 Lobsterfisherman 2012 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.
On paper these two are close siblings in the size department - Eastern 27 2008 at 26,0 ft versus Eastern 27 Lobsterfisherman 2012 at 26,3 ft. At 4 800 lbs and 4 900 lbs respectively, both sit in a similar weight class - either should pair comfortably with most mid-size SUVs and half-ton trucks, though always confirm your specific tow rating with the motor added.
The power gap is worth calling out. Rated to 300 hp, the Eastern 27 2008 has a 75-hp advantage over the Eastern 27 Lobsterfisherman 2012's 225-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Both carry nearly identical fuel loads - 110 gal and 110 gal - so range won't be a tiebreaker here.
Both boats are rated for 8 passengers - a good fit for a family of four or five plus guests. Comfort at capacity is another matter; the longer hull typically means more seat options and better weight distribution.
Bottom line: Performance buyers should lean toward the Eastern 27 2008 and its 300-hp ceiling. If fuel economy and quieter running matter more than top-end speed, the Eastern 27 Lobsterfisherman 2012 with its 225-hp rating is the more economical daily driver.