I think you got some good advice in this thread. But here's my randomly arranged thoughts...
The other thing to consider is that you added pressure drop in the oil system by adding the cooler. If you add a thermostat on top of that, it'll be additional pressure drop. Its not just the oil temp to the bearings to consider, its also the oil pressure to the bearings. At lower rpm, the oil pump will struggle to deliver the right pressure/flow especially as you add more restriction.
Interesting idea. The oil cooler holds 150cc of oil, and instead of filling the conventional 2.0 or 2.1 quarts for this bike (different literature suggest two different numbers), I filled to 2.25. Since I basically added another 150cc of oil to the total volume, wouldn't I have the same pressure?
Also, normal oil cooling flow (without the cooler) on this bike is to take the output from the bottom of the engine's sump/pump system, run it right up to the top of the frame under the gas tank and into the frame, then let it trickle/sit in the hollow frame as the bike frame is passively air cooled, and the oil is gravity-fed back down to the bottom of the frame where it is then sucked out, filtered and reintroduced to the top of the cylinder head.
With the new cooler, the output from the bottom of the sump/pump is piped directly into the oil cooler first, then ran up to the top of the frame and the internal reservoir and on through the rest of the system. Could this then mean that the lower oil temp in the cooler creates
increased pressure on the oil pump?
The head is the hottest component on the engine, so it doesn't really reflect the oil temp to main & throw bearings, under piston squirt, or cam bearings. But you still don't want the hot head degrading the oil prematurely and wearing out valve seals.
Air cooled engines have to be designed to run at a wider range of temperatures than a water cooled engines. So either way, a properly designed engine should be good to go, but if you are in a hot environment, then it was probably a good idea.
Gotcha. Sounding more and more like it's a great idea in AZ when we go out to play in 90+ temps, but a bypass switch might be in my best interest. Again, more data will be key here. Need to find out the actual oil temp rather than the cylinder head temp at the oil line.
The manual might have been written before the latest standards came out or could be tested.
This statement is directed towards the totally unrelated Tiger and the synthetic oil API/JASO standards discussion? The only reason I brought that bike up was to counter the idea of synthetic oil in a 21 year old dirt bike.
You might also consider a thermostat for that external oil cooler. Check with the place you got it, they might have something like this to fit:
http://vwparts.aircooled.net/Engine-Oil-Thermostat-p/oil-thermostat.htm
Covered in the OP.