I always trail with motor up and sitting on transom saver. I travel some really horrible little roads to get to the lakes around here and if the axle goes down in a big hole the motor would be dragging on the ground if it were down.
I have a 1987 Lowe 14 Skipper. Same exact measurements as yours. Seems a little narrow to me also. I Haven't had a chance to take it out since I got it so no idea about the stability of the boat.
Economy. Over the last few years, downsized from an F350 towing a 26' cabin cruiser to a Nissan towing the little tin boat. Lots less strain on the nerves and wallet.