Only reason i am considering this is ive driven duallies as daily drivers for well over a decade now, just recently got the 1/2 ton eco diesel. In reality the dually is no big deal to drive around, but is absolutely over kill for 95% of the year and i suppose really a 3500 srw would be as well, but it would be i think a far more reasonable vehicle to daily drive in comfort and still have somthing to pull our camper around... kind of a compensation on either side of the scale. And really, i love my 5.9 but the old dodge cabs arent terribly family friendly especially the quad cab.
and in all honesty the braking cant be any worse on a 18 and up 3500 SRW compared to my 07 5.9, thank god that thing has a super agressive engine brake and a standard trans.
as for the boat yep it has garbage hydraulic brakes, i think they worked for about the first month of ownership.