Should I get another truck as a TOW RIG?

[fishmunger]

Hey guys, need some advice.

So right now I have a 64 short fleet that is pretty much a rat rod. It's lowered with a c-notch, has PS, P discs, and a built 350/turbo 400 with a lopey cam. It's fun to drive, handles pretty good, everyone likes to look at it, but it gets ****ty gas mileage and doesn't tow very well. But it's fun, and I love it. I got it in high school, and I think I'd regret it if I were to sell it. I daily drove it for 3 years, but in the last 3 years I've been daily driving my 2003 GMC Sonoma (which looks lame). Kinda sucks to see the '64 sit but it just isn't practical to drive around.

So now I'm at a crossroads. I'm thinking of getting a new (as in different, not "new") truck for my towing needs. I recently built a boat for my business (commercial fishing). The boat is 20' long, fairly tall (has a stand up cabin-so it catches wind when towing), and weighs about 3500 lbs with the trailer. Now, my Sonoma is rated to tow it, and does just fine for the most part, but I'd like to go to a bigger 3/4 ton truck. My theory is that a bigger truck would get pushed around less by the boat and stop better. I'll be towing quite a bit, at least once a week, anywhere from 30-200 miles round trip. So I need something reliable, sturdy, that stops good. Do you think an old truck can meet my needs?

So I'm thinking of selling 1 or both of the trucks I have now and getting something else. I don't have the space for 3 trucks, so adding another is not an option. My sensible side says I should sell the Sonoma, and buy a mid 90s silverado for cheap and use that for towing my boat, but I hate looking "normal". I want to look COOL!

Would I be crazy to sell my Sonoma and have 2 old trucks as my daily drivers?

I've been considering making my 64 into a daily driver by putting a more efficient motor/trans into it...but I wonder if that is worth the time and money? And maybe I'd be sad down the road if I didn't have a "hot rod" to play in?

If I were to get a 3/4 ton LB, would a 4x4 be better or worse for towing? I sure would like to have 4x4 too...

Well, I'll stop for now...thanks for reading...anyone care to humor me?