Well, Steve ... I'm part owner with my son in an '07 3500 6.0 Vortec with towing package. Extended cab, clamshell rear doors ... full 8' bed. BIG mutha!
My son picked it out ... went from a '94 Dodge 2500 V10 ... he likes "real trucks"

He shopped them all, and decided that the GM line was the best available thru '07.
Vortec is LS architecture, but Iron block.
'07 has 6 sp automatic, so it works ok with the 4.10 gears of the towing pkg.
He's had it since end of July ... but it's errands only ... I just drove it around the block once ... but we opted for the 3500 over the 2500 for the extra margin of capacity (extra rear spring). When I use it, I'll be towing a trailer ... dunno if it will be enclosed or open. We opted not for the diesel or dually as it is not going to get high miles or sustained heavy towing use.
My gut says for a lot of towing, the 2500 series is better ... for your intended use, the 1500 may be fine.