Both the Checkmate Convincor 270 2009 and the Checkmate ZT 244 2011 are deep-V designs, both built in fibreglass, so the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?
On paper these two are close siblings in the size department - Checkmate Convincor 270 2009 at 27,0 ft versus Checkmate ZT 244 2011 at 24,2 ft. Weight tells a clearer story for trailering families: the Checkmate Convincor 270 2009 tips the scales at 4 000 lbs - 250 lbs more than the Checkmate ZT 244 2011 at 3 750 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.
The power gap is worth calling out. Rated to 525 hp, the Checkmate ZT 244 2011 has a 100-hp advantage over the Checkmate Convincor 270 2009's 425-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Checkmate ZT 244 2011 carries 80 gallons versus 75 gallons in the Checkmate Convincor 270 2009. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.
Bottom line: The Checkmate Convincor 270 2009 at 27,0 ft is the right call if deck space, comfort, and entertaining are top of your list. The Checkmate ZT 244 2011 at 24,2 ft wins on trailering ease, likely lower purchase price, and simpler docking - a solid choice for a buyer who wants more boat for less money.