For trailering, the Four Winns 214 Funship 2005 has the edge at 436 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 214 Funship 2005 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.

The Four Winns 245 Sundowner 2004 has the bigger tank at 65 gallons, versus 5 gallons on the Four Winns 214 Funship 2005. That 60-gallon difference translates to roughly 180–300 nautical miles of additional range at cruising speed, depending on motor, load, and conditions.

Yes — both the Four Winns 214 Funship 2005 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.