For trailering, the Four Winns 244 Funship 2006 has the edge at 47 lbs dry weight versus 445 lbs for the Four Winns 245 Sundowner 2004. Add a motor (typically 300–500 lbs for an outboard in this class), gear, and a partial fuel load and the difference grows. Lighter is friendlier on smaller tow vehicles and on fuel economy while hauling.

The Four Winns 245 Sundowner 2004 has an official capacity rating of 8 people. Capacity data wasn't available for the other model in this comparison — verify directly with the dealer.

Both the Four Winns 244 Funship 2006 and Four Winns 245 Sundowner 2004 share an 8 ft. 6 in. (2.59 m) beam — meaning both sit right at the 8’6" threshold that most US states use for standard-width loads. In most states you can tow at that width without a special permit, but regulations vary. Always check the rules for your state and any states you'll be passing through before your first long haul.

Both boats carry similar fuel loads — 65 gallons and 65 gallons respectively. Range will depend heavily on motor choice, throttle usage, and whether you're on flat lake water or coastal chop.

Yes — both the Four Winns 244 Funship 2006 and the Four Winns 245 Sundowner 2004 are built by Four Winns. That means shared dealer networks, common parts availability, and consistent build quality across the line. The choice between them is essentially a question of how much boat you need, not which brand you trust.