Hello to all,
Your opinions are appreciated. What do you think could cause this roof to do this? Or do you think it is just a plain bad install by looking at the first two pics? I think the last pics just show the lack of flashing. Your thoughts? Thanks to those who reply.
With the wierd windows and paint overspray, I’d go with a bad install.
I bet they got windows, paint and roof all done by the same company.
I’ll bet it’s a flip…
The shingles look as if the nails weren’t long enough to hold, why it would lift like that looks like the flashing in that area is lifting or are those shingles and not metal in the transition area. Could have been that new gutters were installed also in that lifted up area. Or if they installed a new roof they may have been lazy and not insert the shingles under the gutter.
The valley is a poor job of a tight closed valley install or did they try to interlock the T locs some how? Never seen that done here in Colorado.
The siding is to close to the shingles and are you sure there in no step flashing that you might not have been able to see under there.
Any case trim the siding back and make sure there is step flashing and a GREAT paint job on the siding.
Is that two layers of roof covering?
Gregg;
The guys are on the ball here with good advice.
You need to start inspecting newer ones. ha. ha.
What I saw, if it helps.
Bad install is an understatement.
sheathing missing or not continuous at gutter area.
8" Masonite siding.
two layers of roofing possible
No drip edge
T-lock asphalt roofing
siding to tight to roof and unable to inspect step flashing
Masonite siding observed as 12", 8", 6", what’s up
Home Depot spray gun, ha. ha.
Wonder how many cars in the neighborhood have that color.? ha. ha.
Marcel 
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Hey Marcel,
Not sure what you mean by the masonite siding (12-8-6?) Composite siding like that is the most common around here. T-lock is also very common. Not so common where your from there in Maine?
Comment was made from your last photo that appears to indicate an exposure of the siding from approximately 12"-8"-6".
Just caught my eye and curious as to why since I don’t see the whole picture as you did.
Good job Gregg, keep it up.
Marcel 
I thought pics 4 and 5 should have had visable flashing to divert water away from the siding, especially from the fine job on the gutter above!? Your thoughts anyone?