Dry trailer at 5595 will translate to the ballpark of 7,000 loaded. If you put 13% on the hitch (reasonable for a bumper pull) that is 910 lbs. Add 100 lbs for the hitch and sway bars and you are at 1010 lbs.
Now take a look at the payload sticker on the door jamb of the trucks you are interested in and see how much payload you have left for yourself, passengers and whatever you want to carry in the truck. Also pay attention to RAWR (rear axle weight rating). You may choose to budget a little extra to give yourself some room. This may help you decide what truck will work for you.
If you go the 1500 route make sure it has a tow package with a transmission cooler and a larger radiator. LT tires are much nicer for towing.
Good luck,
Stu