Real problem is too many toys you want to take with you while make the DW happy. Solution is to limit yourself to one of three choices: TC, TC w/boat, or DW w/Nash.
The super charger on an engine not designed for it and used for towing is going to equal trouble. First will be over heating issues because the radiator isn't big enough, than transmission trouble because the cooling and bands are designed for the power, etc. Be cheaper in the long run to buy a new truck.
Alternative would be to buy an older diesel truck for the few occassions when you want to take the Nash and boat. (oh yeah, the DW but why? j/k)
P.S.
Nice mid-life crisis to have. :)