It's never a good idea to idle an air cooled bike for more than a minute or two on really hot days. If you find yourself sitting at long lights, or in traffic jams in those scenarios, shut the bike off for a bit. Even moving at just a few mph is enough to prevent most air cooled engines from overheating, which is why the lane splitting Big Bird mentioned was implemented, allowing bikes to filter through stopped traffic at a slow pace to keep them moving.
Bear in mind that the oil cooler only really works when moving, so if you end up sitting for extended periods of time, shut the bike off. The oil coolers do a great job of shedding that built up heat once you get moving far more effectively than the engine case alone though, so they are definitely worth it. I can usually judge how hot my oil is getting by the feel of my clutch (clutch fade) and generally I have noticed that once I get moving a couple of blocks at even 15-20mph, the cooler has already started to do it's job.
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