I have the HD oil temp/level dipstick as well. I used to worry about the temp on mine all the time as well. Now I just check it to see if the oil is low. The temp was always in the 250- 260 range, never seemed to be a bother.

 

Put an oil temp guage in my fairing and sitting still will sometimes see it up at 230, but rarely higher, and as soon as I am moving again, will drop down a bit. However, I do have an oil cooler, which I think was nice that they started making that stock.

 

If the gauge is accurate you should be concerned. You should never run that hot even in gridlock traffic.

Yes. All TC engines need coolers, IMO. If you really want to nip the heat issues in the bud, install an oil cooler and a Ward FCS fan kit (already linked). The latter has kept my head temp. in control for one year through a summer in S. LA, and the front head typically stays <235° (250° max) with oil temps <200° (225° max). Not once did EITMS (set to 290°) kick in all last summer, and didn't even come close. The head is the hottest part of the motor and if you can control the heat in that area you are one big step ahead of high oil temps. I would say if you must make the decision of buying only one of the above, go with the FCS first.

 

I added the HD oil cooler to my 07 Ultra. Definitely brought temps down below 220 consistently, even on a hot day (90+) . Not gonna help much while sitting in traffic or a long light though. Easy to install yourself if you're mechanically inclined and have the time. The heat these things put out is unavoidable. Even my 00 Fatboy will get toasty on a hot day in traffic.

 

Thank you all for your suggestions. I tried a used oil cooler, darn thing leaks (I think it's leaking from where the filter to the adapter, but it's too tight in there to be sure). Took it off, and added the JES Custom.
Probably going to get Ward's FCS. I'm sure it's good, but don't quite like the look. It kinda doesn't "flow", and they look "in the way", if you know what I mean.

 

I've got Jason's fans on my bike. They aren't in the way. I only turn them on in traffic.
Contrary to popular belief different oil will not affect temps. In fact thinner oils dissipate heat faster than thicker ones do. And going from conventional to syn won't help oil temps however synthetic oils do have a higher flashpoint,which is better when extremely hot.
I got a 10 row jagg oil cooler. I love it. With Jason's fans and that oil cooler my oil temps never break 220,even when stopped in traffic and not moving at all.

 

I think once the FCS is installed you'll be fine with the appearance, and when you notice the improvements in cooling I'll wager you won't have any second thoughts. One thing for sure is that the FCS will get you plenty of comments, mostly people asking what they are. Jason offers three finishes, I think--chrome, black, and gray. I think black fits best and allows them to blend into the engine better visually, but that's just my opinion.