D-Ring Fitment

The stock aftermarket polished D-rings are usually a tight fit over the Pan covers. Not good. The D-rings bind at the corner bends and sometimes along the sides on almost all of the AM (aftermarket) covers. The inside walls of the D-ring ned to be dremeled away until the ring fits looser on the cover, which might allow some of the screw holes of cover, to drop though and stay plumb (straight up and down).
Any thread-stress to the D-ring screw holes in the head is instant damage, and if the screws are cocked because of the cover holes are eclipsing the D-ring holes, even the least bit, it will be hard on the head threads.
The fix, is to dremel out the cover holes to match the D-ring holes.

The covers are the problem (Paughco even). Elongating the holes to match the D-ring would seem the only way, but bad, if the screw holes at the ends of the cover require elongating into the cover cavity (since the holes at the end of the cover are already near the interior edge of the cavity) - promoting future leaks.

It's a known problem these cover holes. I looked at the '07 V-Twin catalog and they have replica stainless covers now, with the caption "...produced by New Tooling for exact fit and shape".
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I talked to Paughco and they said ".. some of the holes have been off for a long time. There's a few of the holes you have to open up some, and the covers will fit".
11 of the 12 holes are eclipsed on mine.
I put the d-ring and cover together and stuck screws through it, looked at the bottom to see on which side I needed to remove material and Sharpie-marked only the half radius of each cover hole that needed it, then dremeled the holes (with lots of fitment sessions in between grind sessions).

Look at the screw on the far right. See how close it is to the interior (cavity)? When you have to dremel a hole inward, you risk creating a potential leak later. That transition radius (at the apex) of horizontal to vertical, is known as a "crown weir" (trap seal dam) in plumbing.

I used a magic marker for Dy-Kem and then pushed the d-ring down on the cover and the places it was tight removed the pen mark. I removed the mark with a wide swath from a dremel cylinder-shaped stone. Where one D-ring screw head would hit the side of the cover, I used the 1/8" spiral burr inside that one D-ring hole and removed some material. The screw head would then clear the cover's exterior sidewall.

Hogging-out a few of the d-ring holes, in addition to whatever cover holes needed hogging will allow cocked screws in a complete assembly to be pllumb. I found that the d-ring holes at the tight-radius bend on each ring need hogging outward, or else the top rim of an OE sylte (1/4" flanged head) screw would hit the exterior cover sidewall,

and still bind at the cover hole that was already at it's limit of hog-out, before it went over into the open cover area and could create a leak at the cork gasket seal. The d-ring hole in this case needs to be hogged outward as shown by the mark (but only slightly, the big mark is only a direction indicator).

The end result is, the d-ring should slip over the cover with no binding, and when you pick up the ring and cover, with all 12 screws in position, the screws should drop-through on their own weight.

The cover then goes on the head with all 12 screws easily hand-tightened with a 1/4" nut driver.

You can start the screws into the head a few threads, with the cover and ring and cork gasket assembled; then carefully lift the ring and cover assembly a little and you can feel where the cover might bind as it clacks against threads.
~ The cylindrical stone removes the high spots inside the d-ring. The spiral burr (above) hogs the cover and d-ring holes. ~
Note: Even though the screws drop through the cover and start easily, once the shank portion of the screw enters the d-ring holes, all bets are off.
Installing the screws and finding one or two tight sometimes can be remedied by hogging out another suspect d-ring hole. Look at where the screw is position when it starts to bind, and mark which side of the hole to hog. [Note: You would never have to remove as much material as is indicated by this black mark. It's a fat mark to mark the spot only. Proceed with caution, a little material removed is all that's necessary.]

Well, between June 20th and today we lost some posted material that took us to a replacement set of Pan covers from CCI (genuine jobber-specific Taiwan), purchased from Kick-Start M/C Parts. The Paughco covers were ruined by moving the flange hole too far into the interior of the cover. These CCI covers have holes that all line up pretty good with and AM or OEM D-ring and only a little cleaning up inside the cover holes will be necessary.

You can see though, that the cover and ring are binding a little on the left side, and that a corner radius screw is binding. Don't try and turn it, the chrome will scratch. This particular screw on the radius can be made to drop plumb, by hogging out the D-ring hole a tiny bit, outward, which will provide clearance for the rim of the screw head. The binding left sie can be cured by cleaning up the cover holes with a Dremel burr.
The CCI covers have a ripple in the flange, but the holes all line up.

The Paughco cover had no flange ripples, but 11 of the 12 holes were all misaligned. I ruined the cover by cutting into the cavity on the radius bend cover holes.

This is not a true reading, since there is chromed hole-slag and blips on the flange hole bottoms. The cover will rock about .012" front to back.

There's a spot where no matter which way I rock the cover, I still can find .016" of clearance.

I'm going to file or grind the bottom-blips from the flange holes; tap flat the rippled flange, and then dy-kem the bottom of the flange and put a piece of emery cloth on flat concrete and grind until I remove a continuous line of marking pen. Not the best method, but flatter than received is my goal.