Up until this summer, I used a small fiberglass dinghy. It has a pointed, but bluff bow, a flatish bottom. We towed it for thousands of kilometers with out major problems. There were times, with following seas, where it would scoot along beside or just about parallel to our boat, and then get caught by a wave and pulled back in line. The conditions were nasty, and we fully expected to loose the dinghy in the middle of Lake Huron. In the end, it survived, and I still have it.
This summer, I purchased a compact RIB (hard bottom, but fold down transom). Much more stable, and much more capacity that the old fiberglass dinghy. Perfect for getting us and a big dog around. But, the first time I towed it in a moderate following sea (waves <2'), it quickly started a taking little water over the bow. Once there were a few gallons in the boat, it would start to take on more as it went down a wave, the water in the boat sloshed to the bow, and thus weighed it bow down as it hit the trough of the next wave, at which point a bit more water would come on board, just over the bow.
It didn't take long before there were 100's of lbs of water and I had to take a break and get aboard and bail it out. Not much fun, and a little dangerous. After that I tried different tow lengths, but ended up with it very close to the boat (10-12') to avoid this problem.
I was surprised at the way it handled. Makes me think that it really needs to be on the foredeck for any real passage making, and towing is for when you are really confident the conditions will remain manageable. Perhaps it is the RIB design?