I ran 16.5's on the rear of my 59 Burb with a Dana 60 8-lug rear end. Once the beads are seated on the rims, they really don't give any problems, but getting that tapered bead to take air and seal up is a real adventure. I used a can of starting fluid and a match, like we did on the 14.5" mobile home tires and the 18-wheeler 22.5" and 24.5" tires. Give the inside of the tire a short squirt of starting fluid, wait about 10 seconds, and toss a lit match at it. Stand back, or get ready to lose most of the hair on your forearm. As soon as the bead seats from the bang, put air pressure to the valve stem.
A safer way to inflate tapered-bead tires involves a 10-gallon air tank with a 2" ball valve attached. Fill the tank to 100 PSI, aim the nozzle at the gap between the tire and the rim, and yank the ball valve open. Wear ear protection; the noise of the rush of air is impressive!
Tapered bead tires were developed to aid on-the-road tire changing, as they don't require any sort of machine to break down the beads. Just deflate the tire, and the bead separates from the rim. A couple of long pry bars are all that's needed to do a change on the shoulder of the road.
Jerry