2000 XLH sportster bike starts up and idles right but once you put it in gear and try to ride cuts out and dies

sounds like it could be a ring problem possibly

Fuel pump? It might not have enough flow.

clutch and kickstand lockout switches need checking...it thinks you are trying to ride with the stand down...

the igntion module on the right side of the motor is probably bad its a typical issue with sportsters, if you heat the area around the timer cover with a heat gun and then try to start the bike and it wont start then you know its the ignition module on the sensor plate.

You need to tear the motor down, sounds as if the pistons seized or you broke a connecting rod, or bearings went out.

In any case you need to have someone that knows what they are doing check it out for you.

Btw, I’m available to help over the phone in case u need at https://www.6ya.com/expert/sean_54c3a3dc48a7773c

Okay one issue with many of the Sportster models is the intake gaskets. They only seem to have a life of two to three years. What happens is once the bike gets warm these gaskets don't work well if very much at all and the bike is too lean to start. But once the bike cools off all is good. Sound familar?
Now I've personally owned a 1978 XLCR, 1984 XLH, 1997 XLCH, and each and everyone has made me cuss with the same issue.
You may have other issues but I would start there first, as the gaskets are less than $10, the labor if you do it yourself is free. Good luck and let us know if this helps.

JP

Could be the coil. Borrow a buddy's coil and test your bike, If not an option buy a new coil.

It sounds electrical and as it's a Sporty, I suggest a temperature-related dry joint opening up in the wiring. One popular candidate would be the earthing strap. It's worth checking continuity with a VOM when engine is hot. It may have a vibration crack. 66C is quite cool for a sportster oil temperature, so I guess you have this problem on every long ride? Good Luck.

Check the voltage at the battery w/ a voltage meter...4 bucks at Harbor Freight...I doubt you have enough voltage to spin the starter. To prove my point put some jumper cables on the batt hook to a 12 volt source, cycle ,car,truck (engine off on donor veh)..should fire up..check tightness of all batt connections...I had a battery die right in the middle of a ride one time,and it was a harley....so if it starts w/a jump, time for a new batt...good Luck to you friend.....Tim