KMB,
Just my opinions, but here they are anyway. Be careful not to option your way out of price range, any of the tandem utilities will do the job for you. The angle frames with 1 foot side frames use lighter materials and use the side as a truss to gain strength without excessive weight. This helps keep them lighter than a flatbed. Anytime you add trailer weight you take away load capacity. I know that some talk about flex too, but if you look at the big aluminum flatbed semi trailers, they really flex! On any website you can get into bigger is better, but stay within the constraints of the tow rig and you will be happier. You can get a heavier trailer down the road to pull with the dually diesel when you get there.
One other note, don't buy a heavy single axle trailer!!!! The tandems smooth things out so much, extra safety with four tires,if youve ever had a tire failure on a loaded single axle you won't want one. More brakes, much less jigging on your truck hitch, pull more weight with less drama.
With the half ton you can haul 7000 on the trailer axles and 700 on the tongue weight, giving 7700 total, minus 2000 for the trailer, about 5500-5700 net. Thats enough in my opinion.
This is just my opinion and I don't really want to debate with anyone on their 27 foot gooseneck brake free 30,000 lb behind an S-10 :hmm3grin2orange: