Bonnewagon, ever heard of Zymurgy's Theorem? "The only way to repackage a can of worms once You've opened the original container is to use a larger can?" That about describes the ongoing discussion between the chain gang and the belt brigade.
When belts first came out for the second time in the early/mid 70's the biggest problems was finding replacement belts that would fit the drive system, and belt longevity. Any kind of debris, dust, dirt or small granule material that got in between the pulley teeth and the belt could cause the teeth to be damaged or the belt to shred or tear. Engineering evolution in the belt materials and the metallurgy of the pulleys over time has mostly cured those issues. What hasn't changed is the need for maintenance. Belts do need to be periodically retensioned and the process can be complicated, time consuming, and require special tools to accomplish. Belts are cleaner' they don;'t need regular chain lube application, but keeping them clean can be just as much an effort. And they do have an operational life.
The chain, and its matching chain wheels, by contrast, can tolerate being exposed to climate and weather for a lot longer longer than belts. A chain on a country road is more or less operating in an environment that is absolutely familiar and mostly old school. Setting and cleaning chains has to be done more often because they will stretch and leaving them loose will cause roundover on the chainwheel teeth but the actual process does not need special tools and can be done even if the bike is on the ground, as opposed to having to be in a service bay for belts.
I just did the rear chain drive on my Electra-glide and, apart from the bike lift, the tools I needed were right there in my roller cab. I actually could have gotten away with just doing the chainwheel swap from the wheel coming off to the wheel going on and rehung the chain but elected to go the extra inch just because I was there and could do that bit more work just as simply as not.
As for shaft drives, they are arguably the oldest final drive system that can be found on motorcycles. The best version I ever got to see was the 45 degree transverse mounted Honda? that ran a shaft drive. Altering the engine location from North/South to East/West solved a lot of power transfer issues and having to use a ring and pinion in the rear hub was just the factory concession to reality.
So which would I go with? I'm AMCA; most of what we tinker with is either belt drive, leather belt that is, or chain, with the odd Vintage Euro-shaft system in there to confuse the issue.
Belt would be the best in terms of least necessary maintenance required in the short term' and most expensive in terms of end of life cost attached to replacing and aligning the belt
Chains need more and more regular attention; cleaning and chain spray lube and keeping an eye on the stretch and adjustment for it but, that said, can last as long as a belt and be changed out at the end of days for far less in $$$.
Plus which I am a closet Luddite, and prefer to work with OLD if for no other reason than a perverse sense of satisfaction at seeing the looks on peoples faces when they come up close and personal with old age and treachery and suffer a complete brain freeze, so I will go with what I know and learned on, the chain.
Oh yeah, you don't see many belts on the Vintage and Antique Trans America Rides, unless they are leather, but chains? You betcha.
Nick