The previous owner apparently hacked out a piece of the door. How should I fix it? If I use wood filler, what's the best way to mold it so that it's square? Is there a better fix? (I don't want to replace the door.)
Wood – How Do I Repair this Door Damage
doorswood-filler
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Though the crack is diagonal it looks relatively straight. In this case I'd take a piece of wood the approximate thickness of the crack at it's widest, cut it to length and then taper it so that it fits quite snugly - you should have to use a mallet to tap it home. Don't worry about the thickness too much - but obviously it should be fairly close.
Once this fits use wood glue to bed it in and fill the imperfections, though you might get a better finish using wood filler for this. Basically put more glue in than you need so it gets squeezed into every nook and cranny. Clean it off before it sets, then leave the repair to set.
Once set use a chisel to remove the excess from both sides of the panel and finally sand to make it flush with the panel. Fill any remaining (and hopefully small) holes, prime and paint.
By making the fit tight you minimise the chances for it to move, and therefore crack, further.
Since you say that the wood under the hinge and around the hinge screw holes has split and gone soft it pays to check the wood of the door jamb adjacent to the hinge mount location as well. If the wood there is not sound then you are likely looking forward to some more serious repair such as replacement of the jamb side board or the whole jamb.
If the adjacent wood is still in good condition it may be possible to cut out the the piece under the hinge plate and replace it with a new block of wood. Edge gluing of the block of wood into place will require a very close tolerance fit and ability to clamp it into place to get the strongest joint possible. The best side for the wood to bond well with the new piece is along the grain so make sure the insert piece has the same grain orientation as the jamb. Then you can clamp across the jamb and to do so it would be necessary to remove the casing trim along the hinge side.
I would not drill out and chisel the the opening to shape as it would be a lot of work to get the tolerance necessary for a decent wood glue bond to the insert piece. Instead I would use an oscillating multi-function power tool similar to that pictured below. Using the plunge cutting blade like the middle one pictured it would be easy to cut out the damaged piece from the jamb with nice straight and square cuts.
Once you have the new piece glued in place and you go to remount the hinge make sure to drill appropriate pilot holes for the hinge screws so as to avoid splitting the insert wood piece.
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Best Answer
Assuming this is an interior door, I'd just scribe the top of the door parallel with the top of the jamb and plane it to the line. It actually looks a tad out of square and a bit tight in the jamb.