I don't think any shock or front end system will improve tire wear. Cupping can be cause by poor contact with the road surface, but in the case of our bikes, the cupping problems can be a defective tire. Also air pressure plays a part. But, a good front suspension will keep the front tire from "skipping" across the road surface, as the suspension is better able to respond to irregularities in the pavement. That is just one of the things immediately noticed when installing something like the Traxxion AK-20 cartridges and a really good set of rear shocks. Putting heavier weight oil in the shocks/forks does nothing but make the suspension stiffer and in fact can make the tire contact problem worse, as the thicker oil has a harder time passing through whatever valves/orifices are in the shocks/front end and inhibiting response. The stock HD forks contain an emulator, but that is light years different than a true cartridge.
On a scale of 1-10, with stock being 1 and something akin to Bitubo shocks being 10, I would say the 440 HD are a 3 or 4, at best.
I have yet to hear a single person on this site say that they feel that the money spent on quality suspension components was not well worth it and that they wish they had done so LONG ago. It's one of those things that you just don't realize how BAD the stock stuff is until you have something to compare it to. People think nothing of spending $2000 on cams, and other motor components to increase HP/TQ, but balk at the idea of spending that same amount on suspension to make the ride and handling significantly better.
Thanks for the information and observation from your experience.
The 10w oil did make the bike "feel" better because of all the bottoming out when riding two up. And as far as the 440's go, they were a great deal and I could afford to give them a try. You're right, they were maybe a 20% to 30% improvement to the bike.
But I'm guessing installing either the HD front cartridge kits or the Progressive Monotubes would get me in the 7 to 9 range on your scale of 1 stock and 10 Traxxion.
I can be aggressive when riding, but with the wife riding most of the time we prefer to ride slower and enjoy the view etc. My wife commented that when I traded in my 15k mile '08 SERK for the '09 SERG, that she noticed me running faster in the corners and leaning more. I do not try to do that, but there obviously is a big difference between the '08 and '09 frames, one of the main reasons I traded up. Oh I also feel in love with the arse end when I saw the '09 SERG in Rapid City in '08 Sturgis. I guess I might have traded up regargless of the frame, but since my wife loved the SERK and dislikes the SERG, it had to be the frame and other improvements that I traded up for...

As far as rationalizing the cost of engine versus chassis upgrades and $$$$'s, I'll share my own thoughts on this.
In my mind changing chassis items is hard to get past becuase the MOCO should have made it right in the first place. But engine improvements, read more torque and hp, is a voluntary thing that really doesn't need to be done and it's something you want to do, not have to do.
I know, that sounds totally backasswards, but in my mind it makes since. If I were to want more power I would not hesitate to do it, but for my current riding style and the wife, I'm happy with my warmed over TTS/2" Fullsac upgrade. I'll also say that the totally stock '09 SERG outperformed my '08 SERK with V&H Oval slipons, SE-AC and PCIII and quick dyno. So "wanting" a bit more rumble and less heat was an easier choice than doing the chassis upgrades. But I'll probably bite the bullet and do the chassis modes this winter, but it's hard to break loose the money for something that I should have to do.
Thanks again on the input and sharing your experience on the subject.