Yeah, that bar is shot.
I've been down the dual bucking spike, long bar rabbit hole a few times on different saws, especially this 441c. I am now back to a 20" bar and the original bucking spike. The oversize dual spikes look cool, but have no practical use for my tree jobs. But I'm in Oklahoma so the bark is thin around these parts. It differs based on your location.
Mission drives the gear - meaning, determine what you are doing with the saw. Felling, bucking, topping, limbing. What tree size you cut the majority of the time? If a 20" will do most of your work, stick with a 20". If you need the occasional longer bar, it wouldn't hurt to have one on hand, but I sure as hell wouldn't run a long bar just to run one.
Regarding the HO oiler? My 441c oils a 24" very well, but haven't tried it on anything longer. An other forum member will have to chime in on a 28" and how it oils.
I leave a Stihl light 28” bar with a big clutch cover and dawgs on my 441 all the time, my oiler is opened all the way and it oils just fine as long as the oiler holes on the bar are clean. As mentioned above, the job you do dictates the equipment you use. The 441 lives in my truck, and I usually don’t know what I’m getting in to. Being mostly in the midwest or Allegheny part of the U.S a 28 (or 27 since I run a Stihl bar) can handle pretty much all the wood I cut. I also know a guy who runs two 441s and a 440 that both live with the small dawg/clutch cover and a 20” bar. They cut really well, even stock, and I like how they handle more than one with a long bar. He’s on a horse farm and has a 660 for when he needs a bigger bar. Mind you, my 441 is stock as are his. We’re going to run them that way until they go out of warranty.
I ran an 044 for a long time (until August 2018 when it died a sad death) when I was working on the west coast as a firefighter every summer. It was set up as a west coast saw and I ran a 32” bar on it. Out there, skip chain made sense. In the midwest or east coast, it does not. It was a wrap handle with the big dawgs and clutch cover. When I came back east it went to a 25 or 28.
There is nothing wrong with a stock saw, especially a 441. They do 90% of the work on the planet. The only changes I’ve ever made were to open a baffle on a late model MS460... They were severely constricted. There’s no intrinsic need to modify a saw.