Thank you Valvestem!

 

I also have a 2009 Ultra. In answer to the damage part of your question...no 265 is not damaging your engine (probably isn't doing your legs much good though. All oil (synthetic included) starts to breakdown above 220 (synthetic just breaks down slower). I'll also address this guy's concerns about the harley oil cooler below. Here are a couple of things you can do to help your scooter run cooler:

A. Remove your fairing lowers- This is very easy to do for even the mechanically shy. If you need me to I can even email you the instructions out of the manual. PM me if you do. This can easily be done in 15 minutes. I take mine off in the summer, and put them back on for fall/winter.

B. Ensure your heat management system is turned on.- One of the pictures I'm attaching here is an infra-red pic (Got a pretty neat and $$$ FLIR camera at work!!!) of my 09 ultra engine running, with the heat management system turned on. Note the difference in heat signature between the front and rear jugs.

C. Buy/Install the harley premium oil cooler.- The harley oil cooler (at least the newer ones) have a thermostat that opens at 185 to allow your scooter to warm up 1st. It also has a feature called turbulators that help the oil to exchange heat better. To the guy with the issue of a hole in his line:
1. On my 2009 ultra the cooler lines run between the vertical frame tubes.

2. I went to Pep Boys and bought steel braided line in the performance section ($17 for the 3/8 inch X 3 feet kit) and a couple of extra "dressy looking" screw clamps for it (The kit comes with 2, but you need 4). These clamps make the line connections look like screwed/bolted connections. In reality they are typical screw type hose clamps in disguise. Still, it looks much better than the rubber hose and connections that come with the cooler, and the stainless steel braiding is insurance against holes in your line. I'm attaching pics of this also.

D. Buy/install the harley oil temp gauge- Get that worthless "air temp" gauge out of your fairing.

Hope this helps.
-clutch-

 

Oh yeah...I almost forgot (Don't know how I could have missed this). A fuel management system (I run the Power Commander 5, or PCV) will allow you to richen your fuel mixture, and give you a very slight performance increase. I live in the desert, and am here to tell you, all these things make a BIG difference...not only in how cool your bike runs...but also in how much heat you, and your passenger have to endure!
-clutch-

 

I also have an 09 Ultra with the HD Premium Oil cooler. I run Amsoil synthetic.
In my case, the 2 biggest improvements in engine heat were attributable to
1) a richer map in my PC-V
2) a set of V&H Dresser duals (true duals aka 2-2) to replace the crappy 2-1-2 stock headers. The stock headers are a furnace, particularly around the collector where the 2 head pipes merge before the rear pipe crosses over. Gasses are trapped there and this area becomes scorching hot. Also, the right pipe receives around 70% of the gasses and the left only 30%. With true duals, the 2 sides are 50-50 and the right side is much cooler. the left side becomes a tad hotter but overall, the heat is no longer intolerable. Sound is greatly improved too.
My 0.02 cts

 

I'm running here in the high desert with no oil cooler and no temp gauge. I've had no problems or excessive heat off the motor. Now I'm rarely in stop n go traffic - nearly always on the open road - but haven't felt roasted by the motor and never had the heat management feature kick in. My bike is bone stock. I've been running Mobile One 20W-50 since 5k. I may add the oil cooler as a precaution, but at this point (33k) i've not actually felt like it was ready to melt down.

 

I agree that the motor isn't going to "melt down" on a bone stock bike. If your heat management hasn't kicked in...you either have it turned off...or don't do any stop and go city traffic riding. The fact that you haven't had to endure any motor heat tells me you probably stick to the open road (I try to myself). There is no doubt however that EPA pressure has caused harley to run these bikes too lean. That is one point I haven't found anyone to disagree with.
The oil gauge obviously isn't going to do a thing to make a bike run cooler. Still, I've been a maintenance guy my whole life, so it gives me peace of mind. The oil cooler also isn't an absolute requirement (as are any of the things I've done to my scoot). Still, from a reliability standpoint, all of the things I mentioned before can only help. Especially the fuel management system (PCV) is a benefit to a longer lasting/cooler/better running scooter.
-Clutch-
P.S. I noticed you're a back and forth cali/AZ guy...maybe we'll get a chance at a warm ride and cold beer sometime?