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Drawings of what the building will look like and the headwall detail are in my Album
Folder PDF Files.
I will be doing the roofing. I have simplified the Porch Roof by eliminating the overhang.

So, let's take this step by step...........

Looking at the headwall_2.pdf file:
1. Roof Sheathing will end flush with the siding.
NOTE: The left side of the Building/Porch will have siding. The right side
will not - the sheathing will end at the rafter.
( The building.pdf file shows the side views )
Eave drip edge, roofing felt, rake drip edge and shingles will be applied
in that order. NOTE: roofing felt will run up the headwall the entire width
of the sheathing - 2" up the wall should be sufficient, since the front wall
siding requires a 1" space between siding bottom and roof deck.
( I could NOT show the roofing felt detail in the headwall_2.pdf file )

2. The headwall/apron flashing ( 5" up / 5" over shingles ) will run the length
of the sheathing, as illustrated by the dotted lines in the headwall_2.pdf file.
( To keep it simple, we will not go into all the additional details of the actual
headwall/apron flashing installation.)

3. The headwall water barrier ( tyvek ) material will then be placed over the
headwall/apron flashing. And of course, the remainder of the building.

4. The side wall siding will then be attached ( salmon colored rectangle ).

5. The front wall ( headwall ) siding will be attached 1" above the roof deck
and side wall siding.

6. The side wall vertical trim will then be attached ( yellow colored rectangle ).

7. The front wall ( headwall ) vertical trim will be attached - AGAIN - 1" above
the roof deck.

In the headwall_2.pdf file the "Arrows" point to the PROBLEM area on each side of the building because the roof just butts up against the side wall siding and trim. The size of the area would be approx. 1" H x 3/4" W ( W = sidewall siding & trim )

The only thing I can think to do here is to apply a sealant/caulk over that entire ( 1" x 3/4" ) area and the roof/siding&trim butt joint. What would be the best sealant ?

Is this the correct approach, or am I way off base ?

Chuck - I did like your idea - but thought just eliminating an overhang entirely
would simplify things. Any corner in that area, I think, is just asking
for trouble and a potential leak.
 
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