How often do you tow or wish to tow now?
If you only plan on towing once or twice a year, I'm not sure the added investment of a diesel is worth it.
I have had opportunities to drive my friend's worked Duramax (tuning, no exhaust, no emissions, bigger downpipe, level lift, blahblah) and while it's fun when you stand on it it's a TURD when you're not really into it.
My daily driver is an 06 Avalanche 1/2 ton (5.3) and I'm quite happy with it. I haven't pulled with it yet, but I *never* pull. I did have one opportunity to pull with it but said diesel owner was out of town and loaned me his truck instead. It was a *very* small load (tow dolly + integra), but aside from negotiating lane changes and turns there may as well have not been a car behind me at all.
That said, my 1/2 rides significantly better, is quieter, was a *lot* cheaper and parts costs are obviously a lot less.
If you never plan on pulling >5000lb, I think a 1/2 ton gasser is an excellent choice. If you plan on pulling >8k, I think you really need to consider the diesel. Between those two ranges depends on how much and how often as to which vehicle I'd pick.
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