Coyote Headers

[Tree]

I tried to put on the passenger side header today and I can't get two of the bolts to go in smoothly. They are the two upper bolts farthest rearward. The six others all feed in perfectly. The two will go in smoothly without header in place but it seems like the holes for the header are just off enough that it pinches the bolts as they go in. The bolts are currently in as tightly as I can get them but they are probably both about 3/8th inch out from flush to the header. The header seems to be held in place really well. A small part of me wants to consider it held in place and done but I know that I should keep fussing with it. I tried loosening the other 6 to give room but the two bolts are still just as tight even with everything else lose. Should I pull the header off and drill out the holes to be slightly larger or should I just call it good? Anyone else have this problem and if so, what did you do? The bolts are all tight right now and I am not looking forward to pulling it off and starting over. Also, if I pull it off, do I need to put on a new gasket? The gasket there now has been cranked down on.