I've been changing mine at the end of the season for a few years now. I get the engine nice and warm, change the oil and filter, then go get gas about 1-2 miles away, get home, put my fuel conditioner in, run the engine for a few seconds, and I'm done. I won't touch the oil/filter again until the end of the next season. I'm running Redline oil and an Amsoil EaO filter. No problems yet with two bikes. The reason I run the engine for a couple miles is to circulate the new oil, then I run it for a few seconds after the fuel conditioner to get it into the carb. I don't start the bike during winter unless I plan to ride it. I put it on a smart-charger. In the spring it starts right up. After the first tank of gas I change the plugs.
I'd say leave that oil in for at least 5,000 miles or until the end of the season.