IMO, yes, for exactly the reason you're experiencing now...parts wear and you end up doing it right before it's over with in a lot of cases.
Don't misunderstand me here, as I'm just giving my opinion...the front suspension components on a HD bike are so bad, that simply changing fork oil to a heavier weight only accomplishes one thing...makes the ride harsher/less forgiving. A good front end works just fine with 5-7wt oil...a poor one won't work well regardless. This is one of those things that you don't know what you're missing because you have no basis for comparison. Not everyone wants to go to the top end of the spectrum and put $1400 front suspension on their 35K bike (like the Traxxion Dynamics AK-20 cartridges), but something like the Progressive Monotubes make a dramatic improvement, and you can get them in the 1" lower configuration like you have now. You're going to have the front end apart anyway, so putting the extra $275 +or- into having something you'll really enjoy is worth it...again, my opinion. HD has also come out with their own full cartridge system for the touring bikes, but it's more expensive, and I don't think they have it in a lowered configuration, but I have not confirmed that. And somebody else makes it for HD...I don't know who.
With an '06 SEUC, you've got emulators in the forks, which is better than nothing, but with the Traxxion, you'd notice a 100% improvement...with the Progressive, probably a 60-70% improvement, on a scale of 1-100. It's money well spent, just from a safety standpoint...more predictable handling, vastly reduced front end dive when braking, and a more responsive ride without being harsh. IMO, it's even more important with a lowered front end to put something better than stock parts in, as you've reduced already limited suspension travel by 1", so the need is greater.