Not wearing headsets in any small airplane is not picnic. Even pressurized King Airs are uncomfortale.
If he is a CEO, etc and carries personal insurance, you may need to see what he needs to be covered. Many companies require specifics (multi engine, turbine, 2 pilots). Obviously there is a reason insurance companies require this for personal AD&D coverage...so consider that.
The market is right for an small airplane. $200k will go a long way, especially if he can write a check to a bank. Lots of repossessed aircraft out there, and good equipment too.
If you buy a desireble aircraft, it will hold it's value much better than others. If it were my butt in the airplane...
Multi-Engine Favorite: 58 Baron - $200k or less - but I would make sure my "low-time" pilot was sharp and I might run him through a training event either at a sim facility or better off with an experienced pilot that would go along for a few runs.
...and a very, very, very distant second.
Single-Engine Favorite: Cherokee 6/300 - 6 seats, 300hp, single-engine. 15 of them on trade-a-plane for around $100k.
Not wear headsets? Look for a pressurized aircraft then. Cessna P210. Great aircraft, but I personally would not go that route. Most of us still wear active noise cancelling in jets...