Harleys are dry stump. That means there is no oil stored in the motor, it is pumped into the oil tank.
On the Softail the oil tank is higher than the motor. There is a check valve in the oil line to keep the oil from draining down into the motor when it is not running.
It is pretty common for this to leak especially over a long period of time.
The check valve can be repaired, but if it only happens over a winter storage, I would not worry about it.
A lot of times when you start the motor it will puke out some of the oil, but just make sure you have oil when you store the bike, make sure none has drained onto the ground, start it up, shut it off and check the oil, add what is needed.
And yes you do not want to add oil to the tank before you start the motor unless you like cleaning up oil.
And yes this is pretty normal, well not normal but common