Carb drain

If you pull off the carb drain and the gas is ON then it will just keep draining till the tank is emty LOL, if the gas was off there is a fair amount in the bowl and the hose leading from the tank to the carb, it may seem like it takes forever but it's a small hose.. As far as gas in the air box when the fuel is shut off then it came from what was in the carb and abit from the hose to the carb. Do you have a snorkle on the bike , The vacume effect from the snorkle going through the air when trailering will pull the gas into the airbox. If you have a snorkle just cap it when trailering . Hope this helps

No snorkle and when trailering it I shut the gas off and run it until it dies.

If the gas is shut off and you run the carb dry then maybe the ON/OFF/Reserve valve at the tank is leaking a bit and all the bouncing while the carb is filling up on the trailer is causing it to overflow thus going in the air box . That will also explain why the carb keeps draining and draining. while draining the carb will the valve OFF try pinching off the hose into the carb and see if the flow stops , If it does then the vave in the tank is bad. Or the knob that controls the valve is on backwards and your really on reserve is this possible. Again hope this helps

I did not have the gas off last night when tring to drain it. I'm just going to start keeping an eye on it and see if it's just from not draining it often enough.

A very small amount of dirt in the carb or a sticking float can cause the gas to continually flow from the drain of a flooding carb. That's why it's there in the first place. That's why I leave mine unplugged unless I'm going in deep. Then I just slip the drain hose on over the bolt that clamps the rubber boot around the rear driveshaft housing. I remove the hose later in the ride so the drain can function as needed.

i had a stuck float twice...

easy to fix...

if gas is flowing into the airbox when you turn on the gas, then you have a stuck float.

mine had a little sand in it...

just loosen the big hoses on either side of the carb...unplug all the connections and wiggle it out...pull the top off with the spring and junk...blow it out and then flipp it over and pull off the bottom.
you will see the jet and all the adjustments on the bottom...once everythign is opened up spray it a few times with carb cleaner and let it sit...

then put it all back...good as new.

Do you guys think its stuck? It runs fine now!

Mine always ran fine also. But rarely I would smell gas when the bike was stopped and when I checked there would be a steady stream of gas flowing from the carb drain. I would shut off the gas at the valve and the flow always stopped either before or during the next time I rode the bike.
Took the carb apart and cleaned it. There was dirt in the bowl that had gotten in thru a tear in the rubber around the prime pump. Removed the primer and sealed the opening with a small bolt and o ring because a new primer was $100.00. Haven't had a problem since. Your float may not be stuck right now but there could be a very small amount of dirt that causes it to stick occasionally or prevents the needle valve from seating properly.
Open the drain screw and drain the bowl into a very clean small white container and check for dirt or grit. I would leave the tube unplugged( except for playing deep) so you can see if it happens again.

I really don't go deep, mid tire or more most of the time. When I go deep it's by accident. I hate changing the oil so I try to stay out of the deep stuff. But crap happends ya know.