TLDR - Installed a new door but old door was non-standard size by about 1/4, about 80 by 36 1/4. Added 1/4 strip to hinge jamb but now there is a gap with the weather stripping and serious draft issue with the side. Original entry door was made by Anderson and is really nice, which creates the issue. The piece that weather stripping is slotted into is routed into jamb and head. No good way to remove in one piece. How this idiot DIYer fix?
Longer story is that we bought a foreclosure a while ago in a good school district, most we could afford in the area. I have been working on various repairs for a while and replaced all internal doors (just doors as well as frame on few) with pretty decent success. Our front door was a disaster with dents and terrible paint job that previous owner did, along with other terrible DIY. The door and sidelights were installed by Anderson, possibly when the house was built in late 60s, not sure though. The installation is actually great, all the pieces fit together perfectly and interlock. Unfortunately the OG Andersen door is not standard sizze, its slightly wider than default 36x80, about 36 1/4 x 80. I didn't realize this until I installed the new door (i know measure at least once). There was a solid 1/4 gap, if not larger. To remedy this I added a 1/4 strip on the hinge side and now the door fits nice. It needs slight adjustment but overall I have seen worse.
The issue is that now with the 1/4 on hinge side the weather stripping no longer fits properly against the door, instead there is a gap that has a horrible draft and the weather in MD is only getting worse. First through was that I can just pry out the piece with channel that holds the strip but the piece goes into the head and threshold (see pics 3/4). There is no graceful way of extracting it, adding same 1/4 backing and reinserting. I'm at a loss how to fix this. One idea was simply to add weather stripping to the outside but the wife said it would look ugly, which is far the most important thing in our house. I thought about cutting out the piece of that holds the weather strip at head and sill but dont know if I can reinsert and make it look nice again. Damn you Andersen, your great construction, and non-standard door!