If you have multiple guests on a regular basis..and have no particular afinity to one or the other, I would get a Toon. Plenty of room and a stable platform to walk around on for those guests that don't have boating experience. Great for sightseeing.
If you only need to entertain another couple, a 17-20' bowrider would be a good start...leaning toward 20+ feet.
Outboards are low maintenence when winter comes. Inboard/Outdrives are NOT low maintenance. If you do nothing to an outboard in the fall, to prepare for winter, you will be fine. The water drains out every time you haul the boat out of the water. (Outboard engine in the verticle position)
If you do nothing with an Inboard/Outdrive, the water will NOT drain out and the engine will
Freeze ...As in ICE..and you will be out
Thousands of dollars in repairs.
NB