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Roofing
Poor Flashing Details
This roof counts on caulking and bent shingles to keep water out
The trouble with caulking is that it doesn't last very long. This chimney will need new caulking periodically. Shingles don't make for good flashing. Sure, lot's of folks do it. Lot's of folks have problems with it, too. Eventually, the bent shingle right up against the bricks will crack (like the next picture).
Worn Out Flashing
The roofing material used for this flashing has holes and will leak
This roof also uses shingles to flash up against the brick, just like the top picture. Because the shingle is bent it broke down far sooner than the rest of the roof. The holes are guaranteed to leak.
Since the flashing is the most critical part of a roof, why would you want to use a material that wears out easily? For only a few bucks more the job could have been done right using metal flashing instead.
No Flashing
This roof detail is going to leak
There's no flashing here at all. The caulking will need constant maintenance. It's much easier to just put in proper flashing and not have to worry about it again.