I used to make the trip to my aunts house in Naples, Fla every year. 1600 miles one way. Gas was about 10 mpg on my Jeep Cherokee 4.0L engine. So the cost was about $50 one way in gas. But gas is a dollar cheaper now, so knock off about a hundred from that cost. Single axle Load Rite trailer. Never really had a problem. Never really noticed the boat back there except when braking hard in traffic. Just make sure you carry an extra set of bearings, a spare tire, a tire repair kit, an air compressor and a grease gun. I know several people that have a complete hub, pre-assembled with bearings, that they carry for good measure. It's completely do-able Rob, choice is yours though.
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1987 V20 w/1987 150HP Yamaha on a Shoreland'r Trailer
1978 16.5 Airslot w/1996 120HP Force on a Four Winns trailer
1996 V21 w/1993 200HP Mercury on a Shoreline Trailer
All towed by a 5.7L Hemi Durango.
If God didn't have a purpose for us we wouldn't be here, so
Live simply, Love generously, Care deeply, Speak kindly.
(Leave the rest to God) 
Silence, in the face of evil, is itself evil. Not to speak is to speak, not to act is to act. God will not hold us guiltless.
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