I've been riding an air-cooled TW200 for close to 20 years, both on the road and off-road, generally in hot weather and have yet to have a problem. I run a good-quality, semi-synthetic MC oil though and change it annually.
That said, here is a quick story (well I guess it depends on how fast you read it) about overheating an air-cooled MC. A couple of years ago a friend and I were on a ride on the fire break roads in our local Mountains (near Big Bear in So.Cal.) It was mid-summer and it was hot! We were riding a fairly challenging trail (Clark's Grade) which is largely exposed to the sun as you climb a steep, switch-backed hill. The trail was in poor-condition that day, we were going slow through deep ruts, loose shale and rocks I was mostly bouncing between first and second gears. I've not a fan of this portion of this particular trail so my plan was just to power-through the few miles of hell then take a nice break at the summit.
My friend who was riding with me was on a nearly-new water-cooled Yamaha WR250R and was a couple of bike lengths behind me. About halfway up the grade he starts blowing his horn which for us means to stop, so I did. My buddy rode-up next to me and said "My bike is overheating and yours is too stupid to know it's overheating!" Reffering to the fact that the TW is equipped with three warning lights (Hi Beam, Neutral, turn). My friends WR had many more warning lights, at least one of which was telling him that his water temperature was too high, so we stopped and let things cool-off for a bit, though I don't think my air-cooled bike was nearly as hot as his larger water-cooled one. We still laugh about that today.
All that said I shut the motor off when stopped at R/R crossings. At traffic signals I just let it idle. I actually notice my water-cooled bikes heat-up faster in traffic then my air-cooled ones do. I think oil quality is big factor in keeping air-cooled engines nice and cool.