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The PC fan likely would only be of any benefit when standing still and would probably do more to block air flow once you were moving. On most of the more well thought out bikes that panel already has louvers near the bottom to give it some airflow however without any fins on the valve cover the final impact on engine temperatures would be extremely minor if at all measureable. The real cooling of the return oil comes from the airflow around the timing chain area where the oil pumped up through the cylinder and head returns to the sump.

They earned the Widow Maker moniker with those rickety frames especially on the early ones.

A pretty hot 50cc scooter is the Aprilia or Derby DiTech which are getting pretty common on Craigs List and 55 mph capable. DiTech means Direct Fuel Injection Technology. Pretty reliable unless you tune them to race against 150cc bikes.

With a little work the Spree can make an interesting ride if the speed limitation works for you and they will run on for about forever if you leave well enough alone and keep them close to bone stock.

W650 - You said "I lubed the chain every 200 miles in daily use" which on a motorcyle is at every gas stop or on some with the double sized tanks you'd be stopping halfway to your next gas stop and lubricating the chain.

Fire rescue paramedics that I have spoken too in person tell me that easily 25% of single vehicle motorcycle accidents involve chain failure however they only account for about 3% of the fatal motorcycle accidents since many involve the chain failing while starting off from a stop and the rider falling over from the sudden loss of power or sudden stop if it jambs up.

Sprocket wear - These pretty much exemplify what I have been seeing over the past 40 some odd years:

The motorcycles I have dealt with over the years were all prone to the foibles of chain drives. Chains slinging grease, stretching, breaking, wearing the sprockets thin stripping off teath, etc. You tour on a Motorcycle and you bring repair links and a chain press tool ensuring before you leave that there is enough adjustment left to make it through the trip. Was a problem on the 50cc mopeds and still had to be considered on the Norton Commando 850 that I rode. Riders cope by waxing the chains instead of oiling them, going to double o-rings instead of single, cooking them in a pot on the stove to get the oil grease out and suck the new in as the pot and chain cools. There always seems to be some new wiz bang cleaning system being hawked to help deal with the issue too. Then there is the issue with the rubber damper inside the hub of the wheel that the driven sprocket is attached to failing and having to be replaced to consider too. Motorcycles are not perfect and the multitude of problems one faces with a chain driven motorcycle was one of the design issues Piaggio was trying to overcome when they came up with the first Vespa.

My next door neighbor was happy as a clam in a fresh mud bank when he traded his chain drive for a Boxer Engined BMW sport touring bike with a shaft drive. Those hugh heads sticking out the sides throwing all that heat and such aren't my cup of tea but it is a really silent running bike. I told him to stop talking and breathing so I could hear the engine running the first time he showed it to me and that really wasn't a very big exageration the thing was so quiet and civilized.

Anyways no bike is perfect and you have to find the one that you can best deal with. People though are people and some no matter how hard they try just mess things up when they deal with mechanical devices. In an endurance rally you have to be on top of your preventative maintenance, personal health and have your route and alternates well planned out before you even show up at the starting line if you want to have a good chance of crossing the finish line riding on the bike and not in the cab of a retrieval vehicle.

The scooter I ride is designed for highway running at a constant 75 mph though its capable of more and has a service schedule for oil changes and belt services that basically allows one to ride from coast to coast twice per oil change, 4 times before belt changes and 8 times between valve adjustment checks. Many will mess up and kill a belt prior to that simply by failing to check the filter or by using alternate belts.

Some cause their belts to fail sooner, and I know some will have fits at my even hinting at the thought of this, by changing the contra springs to heavier ones in their clutch which lets face it is going to raise the clamping force on the sides of the belt raising it operating temperature and causing it to wear out more rapidly along with raise the chances of wearing grooves in the drive faces. You cut the cooling fins off the drive face to eliminate rotating mass on the crankshaft (thats really just for short track and drag racing) and again you've shot yourself in the foot and started down the path to early belt failure by reducing clean air flowing though the CVT case. Then there is the crowd that balks at using the correct tools to install a variator and clutch causing their own problems introducing wobbles, etc by setting torques incorrectly, etc. How many fail to perform the simple task of putting a dab of grease in the needle bearings that the clutch idles on? Its all the little details of maintenance that become the big issues with reliability on the road.

The only ones I have heard of are on those where they removed the very reliable OEM variator and replaced it with a Polini. The aftermarket performance variators too often in order to shave weight thin out the ramp plates so that they shatter under the tourque of the high compression 244 engine messing up the splines on the crank. We have found that shifting to sliders and adding a 1 mm machined washer between the outer drive face and the center boss gives a better boost in performance without the failures associated with those less durable aftermarket parts. Trim the excess off the oil sump gasket while your at it to prevent it from being grabbed by the ribs on the back of the belt.

Belt failures are most often from failure to clean the CVT filter then the aftermarket or old belts being used. See that all the time but most don't like to admit that they simply pushed things too far. Lets face it, 12,500 miles from a rubber V Belt squeezed in a variator drive is plenty yet too many push for 15,000 miles and don't make it.

You keep them stock and they are Honda reliable but give you much higher levels of performance per cc.

About 6 maybe more years ago I can't remember if it was Motorbike Magazine or not however they entered several of their senior editors in a Sport bike race but did not tell them until the last minute and shocked them by giving them Aprilia 460, Vespa 300, Suzuki 650, Yamaha and Honda Silverwing large scooters as their race bikes at the last moment when it was too late. One took a place (can't remember if it was the T-Max or Burgman 650) and the rest all finished in the top 20% of the field comprised of 650 and 750cc Sport Bikes. The riders in the bottom 80% really hated the scooters that were out in front of them at the end of the race. They were no longer making fun of the magazine editors riding Scooters in a Sport Bike Race. I really wish I hade saved the printed copy of that article as it was really precious.