Some can quickly learn and master the skills necessary, some never do. IMO that's the reason we see a lot of motorhome owners.
The common mistake that many make is to allow the wife to select the largest and fanciest model fifth wheel she sees. Women rarely if ever understand the fundamental laws of physics at play.
My advice would be:
1) buy a dually or a MDT
2) limit the size and weight of the fifth wheel to 14,000 lbs. or less and remember shorter is better and
3) buy a quality unit, not one with surface glitz and glitter.
There are many RV manufacturers selling lots of units that look good to the uninformed. There are only a handful of manufacturers who build quality units that will provide excellent service for as many years as the buyer wants to use one, is well insulated for all weather conditions, and has good resale value if the buyer decides he wants something different later.
Among the quality trailer manufacturers are Newmar, Teton, Travel Supreme, Alfa, Carriage, NuWa (HitchHiker), and Nash/sorry forgot the name (Grizzly has one). There are a couple more I've forgotten. On this list, many of these names failed recently during the economic recession/depression and are no longer in business but many fine examples of their products are available on the used market.
I won't name the manufacturers I would avoid because many here on TDR own their products and will angrily defend them.
On edit:
Make sure the guy you are advising becomes familiar with the terms GVWR, GAWR, and GCWR as well as tire weight ratings before he buys. Many first time buyers don't like duallies because they are not pretty and buy a large, heavy fifth wheel with a kingpin weight in excess of the weight capacity of their truck's rear axle.
And lastly, make sure he understands that RV and light truck salesmen don't own either product and don't tell the truth.