The asp on mine is a single piece pulley. Its 17ish years old at this point.Will probably go with f250. Have an offshore boat and may go to little bigger boat so will need heavier truck.
Someone is going to get an offroad monster LC from me haha. Right now it's just a bad ass daily mall crawler . Was going to do suspension and tires once back in US. Everything underneath is basically new OEM. Has stock rear locker, tjm front locker, manual trans, part time kit, etc. Hasn't been offroad since I started on performance mods. I did consider it but no way I can hack it up even if I sell for half what's in it (Alot $$). haha
Let me know how the ASP works for you. It has been great for me as an Overdrive pulley. Worth a few extra psi using TRD SC and then Harrop 1.9. Just need to upgrade for engine builder to be happy after balancing crank etc. They don't want a welded pulley on it and asked I buy an ATI damper or keep stock.
All the work in your setup I'd want to keep it somehow but yeah, towing a bigger boat on a first gen isnt the best. My double ski trailer is noticable. You can add power and brakes but that doesnt fix gvwr.
Sean