For five people, I would think a motorhome of some sort would be more comfortable/convenient travel than a truck pulling a trailer. There's a lot more room to stretch out in and a lot more "stuff" available to keep busy with and the ability to run to the fridge or the bathroom more easily.
One other option to consider, if you don't need a fifth wheel, is to pull a travel trailer with a full-sized van. Many of the vans will (or at least can be equipped to) pull pretty large trailers safely (as in perhaps 7500 pounds or so, maybe more), and have enough payload to do so and carry a few people and some stuff without being overloaded. I kind of like the Nissan NV vans myself, but that's purely personal preference.