1) I NEVER wash my chain with water, or soap, or anything except kerosene.
Then it gets coated with Dupont Multi use ( bought several before they changed the flavour).
I always put my bike on the rear stand, start it up and run it in 1st gear while applying Dupont, then run it in 2nd gear and spray the chain from every angle I can. Would not recommend this method, but I trust my Pit Bull stand(s) and haven't had anything go bad yet.
My chain usually gets cleaned ~ 1000kms (at one time was daily) and lubed prior to leaving the house - every time I ride.
I use the soap & water to get rid of the kero so as not to affect the lube.
I've heard rave reviews about the Dupont Multi-Use, however never got a chance to try it before they discontinued it. Good move stock piling!
My concern being anywhere near the running chain is something, anything getting caught in the sprocket... there's many examples of days gone bad. That said, I've run up the bike on the rear stand to dry / warm the chain prior to lubing.
I think you'll find that most lube manufacturers recommend lubing a warm chain which is why I do it upon return from a ride.