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I saw one in the flesh last year. It's a very tidy design but it's in a bad position. The CB300F is about the same money, as is the Suzuki GW-250. A Cleveland Cycle Werks 250 is about $500 less but not as advanced.

I plugged a tire on a 600 pound Kawasaki and it lasted just fine through its service life. I don't know about these new radial tires they have on bikes but I would do it on them too. The darn things are just too expensive to toss without trying it.

The 1974 H1 500E had an improved frame with hints drawn from the 750. It was ungodly fast and handled well with the better tires and shocks I installed as Kevin Cameron noted in a recent article.

I never lubed a chain every gas stop. For one the oil wouldn't settle in. As for the chain I'm quoting, a 1974 Kawasaki, it was long before the advent of O Ring Chain. On my Laconia weekends I did close to 1,000 miles and might have lubed the chain once, at night after shutdown one day. If I did it with a new O Ring chain I might lube it once before leaving and then when I got home after the thousand miles. Cleaning a filter might be easy but the nagging feeling that a belt would fail far from home, on the road, is not a comfort.

If you read the thread on the 2016 Cannonball you saw belt replacements mentioned frequently on a short 4,000 mile trip. Even more amusing is the fact that most of the scooters were trailered to the start and from the finish. If I won, uh competed, with my Honda Rebel I would ride to the start and from the finish. Maybe I would lube the chain at the end of a few days since it takes all of a minute and is cheap insurance.

It isn't just mileage that abuses a belt either. My 2009 CF Moto Fashion needed its Bando Kevlar belt replaced at 9,000 miles with cracking between the teeth a couple of years ago. Of course by then it was six years old and dried out. My 2009 Honda Rebel has the original chain, as does my 1991 Nighthawk and my daughter's 2005 Rebel, and none are dried out and have years of service left. 

Face it Rocky any chain will outlast a belt. Recall that even in the days of non O Ring Renolds chains service life was upwards of 20,000 miles with a little care. Belts are nowhere near that reliable, even today. We won't go into variator failures on a long trip. 

I think you overstate the problems with chain drive. My 1974 Kawasaki 500 triple never gave me a moments issue and it was pre-O ring. I lubed the chain every 200 miles in daily use and did several 500 mile days with zero issues. My O-ring bikes are even less trouble. 20,000 miles of use before replacement are not only easy but expected. 

I'm glad you have had so much luck with your scooter but it's not the norm. Belt breakages and premature wear are the norm with most scooters. My research at Modern Vespa has revealed that despite being so expensive they suffer from many of the same problems that even China scoots do. Constant maintenance, oddball breakages and low overall mileages before unit replacements. Any motorcycle will outlast a scooter under the same use.

My Honda Rebel had its first chain adjustment at 10,500 miles with its O ring chain. My 1991 Honda Nighthawk at only 15,000 miles, admittedly, is wearing its original chain and has plenty of service left. Simple designs with a single carburetor for two cylinders and MSRPs lower than a Primavera 150. Even now a Honda Rebel 300 is almost a thousand dollars less than a 150 Vespa and will give service a $7000 300 Vespa can only dream of. If someone offered me a choice of a BV 350 or a 300 Versys for free I wouldn't even think twice. There is no comparison. The Kawasaki is better built, faster and more durable. And it's Japanese from a company cleaning up in World Superbike.

A good rider can make do with whatever they have on hand. I'm betting those riders would have done far better on motorcycles in that race though had they been on bikes. A scooter still does not possess the balance or power transfer a bike does. I hear that all the time. "I rode my scooter and beat a whole bunch of bikes." Maybe but if you put someone on a track, first with a scooter and then on a bike, his lap times on the bike will always be faster.

I'm sure your observations have some validity but I find it hard to believe that someone who enters a contest like the Cannonball doesn't know about the filter cleaning. They ride under some extreme conditions and I'm more inclined to believe that belts are just not up to the durability of a chain, cogged belt or shaft drive of a motorcycle. It's what makes the Cannonball unique. The scooters are better at short rides because of their limitations while an equal sized motorcycle would fare much better.