People always throw up the blowout scenario... why would tubes increase the risk considering they are encased in a steel belted tyre?
The real issue is being stranded a long way from home with a flat.
Tubeless means you plug the flat and carry on your way.
If you can live with that risk, no need to change unless you're after maximum handling performance.
You SHOULD be after maximum handling performance, unless you don't think your neck is worth it.
With a tube, if you get a tear, all the air rushes out the spokes at one time causing immediate deflation, which can be a big problem at speed. Also, from what I've heard, which sounds plausible to me, the tube causes friction and heat within the tire that makes the possibility of a tear in the tube and a blowout more possible. A blowout with tubes may be a "remote" possibility (unless it actually happens to you) but I don't think you want to crash and spend months in the hospital because of these known problems just to prove to yourself that these problems exist. There is a good reason why 99.9% of the sportbikes made today run alloy, tubeless wheels, the exception being the Ducati Sport Classics and maybe the Triumph Thruxton.
Also, the headshake associated with the heavy stock spoked wheels and tubes is not acceptable to me. Again, that can be a big problem at speed.
Bottom line is that tubeless wheels, along with better than stock tires, are a BIG improvement over the stock set up. Upgrade the suspension and brakes and you'll have a really fun, nice handling bike.
The heavy stock spoke wheels and tubes and retro tires are a distinct disadvantage compared to lighter tubeless wheels and performance tires -- unless your priority is authentic "retro" looks and performance.