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Check out this illustration: Chicago Roofing

Looks to be a modified roof with a silver coat roof sealer. The workmanship around the brick is very poor quality. If you're leak is in that area that will be the most likely cause. The brick area needs to be counter flashed with metal cut into mortar joints for proper seal. Hard to tell...

Definitely need some pics to see what is happening. Chicago Roofing

Unfortunately you need to remove to fix properly. Unless you can seal it from inside the attic. Chicago Roofing

You need to ask for references of other jobs they have done like yours.Or ask if they are working somewhere close so you can see how the install will go.

Make sure you compare each door to one another. You don't want him to trade a good steel door for an inexpensive FG.

It looks like your trim piece is on top of the siding. If this is the case you need to cut the siding so there is an area to place a new piece of trim. Before you put the new trim piece back on, put a piece of Z flashing ( you will need someone with a Break to custom make this piece) under the...