Would like to see what JUST the jugs do by themselves or if you had previously, even though we both know that engine temp and oil temp are two different things.

 

As you eluded to; the love jugs don't seem to do anything to lower the oil temp but that's not what they are designed for.
They do certainly provide some engine cooling simply by the act of blowing cooler air across a hotter surface.

I don't think there's any one thing that is the savior for the heat that these things emit.
I think the best coarse to take is start with the cheapest enhancement and work your way up until your comfortable or until you run out of money.

Here's what I've done to beat the heat;
AMSOIL-
Crotch cooler-
Fuel Tuner-
Love Jugs-
Air assisted oil cooler-

All of the above seem to helped in either lowering engine or oil temp or increasing rider comfort.
But by themselves they each can only do so much.

 

I think that's as good a result as you can get.
A couple things to note...
The oil cooler in front of the jugs restricts cooler air from getting to them. The air that gets to the jugs is now "preheated" as well as somewhat diminished
It looks like your heritage, in addition to the front fairing also has lower deflectors. These will restrict some cooling air to the motor. That added stuff will make the motor run hotter

As a comparison, my 06 Deluxe (slightly smaller motor than your '09) on a 100° plus Central California day will see 210° on oil temp, with a head temp at or near the plug of about 320° after several hours ride time. The difference is most likely due to a freer flow of air around the motor.
My Triumph Bonneville on the other hand, has a factory installed cooler in the same place as yours. A "Naked" bike with an 865cc motor and the bike weighs 250lbs less. The oil temp on that hits 260°. Head temp on that is 375° after several hours on a hot day. Nature of the beast I reckon.

It would be interesting to see what the head temp on your Heritage is. I've measured mine with both a pyrometer with a metal probe as well as one of those lazer temp guns, and both were within 5° of each other. If your head temps are in the high 300s or maybe 400° you would see lower oil temps by doing thing to lower that. Just an idear I'm throwing out there.

 

IIRC optimal oil temperature is between 230° and 260° ... 240 sounds like you're operating in a "sweet spot" ??

 

That is my understanding as well. That's why I'm satisfied with my 242 degree cooled oil.

 

Well I got an 80 mile ride in today with 93 degree outside temp.
The entire ride was a mix of stop and go and open road.

When I got stopped my fans were running and the oil gauge read 231 degrees.
I could differently feel the difference in the lower temp on my right leg which was one of the primary reasons for the oil cooler.

I turned on the Love Jugs Mighty Mites and road another 10 miles home and there was no difference in the oil temp.
However my right leg certainly felt the difference in added heat from the Love Jugs airflow.

Personally unless it's cold outside and I want more heat to warm me up I don't see me turning on the Love Jugs.
The added air cooling of the engine to me doesn't offset the increased heat they create on my right leg.
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I went out today on my 107 Twin Cam Road King; no oil cooler. I run my Wards fans all the time above 60 degrees, no snap switch, just on or off. I rode for about an hour in the curves around the house with more than a few 3 and 4 gear rips to 5500 rpm; the ambient temp was 90+ degrees. As soon as I got home, I parked the bike, turned off the fans and waited one minute. I used a laser temp gun (not from Harbor Freight) and put the dot behind the spark plug and in front of the head bolt (in the black) on both cylinders. Front was 238 Rear was 245. I turned the fans on and ran them five minutes. Front 170 Rear 180 using the same measuring points. The engine was not running during any of this testing.

I turned the fans off and waited two minutes, the temps creeped up a few degrees front and rear but not more than five degrees. I don't have an oil temp gauge so I couldn't tell you what the oil temp was but I would have to guess it was less than the CHT. Just about every oil cooler I've ever had leaked somewhere. I'll ride a motorcycle with a leak or a drip for years without fixing it but I won't tolerate one drop from the pressurized circuit associated with the oil filter. Put me down as a cool the heads and the oil temp will follow but I have no hard evidence of it. Adding a cooler can never hurt, it just ain't for me.

Jason Ward, your work is still good my man.

 

There's no doubt the Love Jugs (Wards equivalent) certainly cools the engine down, but the increased hot air that emits out of the right side of the heads just makes it too hot for my liking.
Now I do have a lower seat and I'm using a crotch cooler so I'll have to concede that possibly my combination may create more of a "heat tunnel" effect.

As for the oil cooler; I suppose the gasket on the oil filter adapter could eventually leak but I don't foresee the high pressure hose fittings ever leaking.
I don't know much about oil coolers but as a mechanically minded person the UltraCool unit is built about as solid as it could be and I really like that there's no clamps involved.

For me thumbs up on the oil cooler, thumbs down on the jug fans.

 

I think it's just a matter of picking one (or both) that you can live with. I have a Corbin saddle on my bike and I can tell you, I feel the heat on my right leg but it isn't too bad because my right foot doesn't hit the deck until I put the jiffy stand down. In the end, I think these engines are a lot more durable than some of us give them credit for and they'd continue to run without either cooling system. I just lucked up on a spare set of Jason's fans here on the forum, I wish I could find a set of silver ones for my old Super Glide.

 

I do not use any coolers what so ever. I just ride for pleasure. No pleasure riding afternoon here! I get up at 4 am to get out if heading east. A little later if going in another direction. I just keep her moving and avoid the super slab and city driving. Works for me. Oh I removed my lowers for the summer and to eliminate rattling noises.