When two boats share the same hull type — in this case both the Gambler Gambler 2100 2008 and the Gambler Intimidator 2000 - Dale Earnhardt Limited Edition 2007 are modified vee designs with composite construction — 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?
Size is the most obvious dividing line here. The Gambler Gambler 2100 2008 measures 20,6 feet overall (2008), giving it roughly 18,6 additional feet of deck space compared to the Gambler Intimidator 2000 - Dale Earnhardt Limited Edition 2007 at 2,0 feet (2007). Weight tells a clearer story for trailering families: the Gambler Intimidator 2000 - Dale Earnhardt Limited Edition 2007 tips the scales at 155 lbs — 139 lbs less than the Gambler Gambler 2100 2008 at 16 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 280 hp, the Gambler Gambler 2100 2008 has a 45-hp advantage over the Gambler Intimidator 2000 - Dale Earnhardt Limited Edition 2007's 235-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Both carry nearly identical fuel loads — 5 gal and 5 gal — so range won't be a tiebreaker here.
Both boats are rated for 6 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: The Gambler Gambler 2100 2008 at 20,6 ft is the right call if deck space, comfort, and entertaining are top of your list. The Gambler Intimidator 2000 - Dale Earnhardt Limited Edition 2007 at 2,0 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.