It's not only not normal, it's just plain wrong. I don't see any evidence of proper flashing in the picture. Is this a single layer of shingles, or was it installed on top of a previous layer? With multiple layers, I frequently find that the 'installer' has failed to address the need for proper flashing.

Lost, In all honesty, there's no way to make a true assessment without an actual survey. However, I think the gap in the shingles has always been there and hasn't caused a problem before now. The flashing around a chimney is an area that requires periodical inspection and maintenance which most homeowners overlook. If the caulking or other sealant where the flashing touches the chimney has separated, water can get behind it and with the volume you are getting, eventually find it's way inside the roof. If getting on the roof is not a problem for you, you can reseal the flashing for pennies. If not getting on the roof is appropriate for you, here's what I would suggest....since the flashing probably needs maintenance, have the guy that suggests that is the problem do the work......with a written guarantee that will fix the problem. If it turns out not to be the problem, he can fix the problem at his own expense. If I were forced to make an assessment....I personally would suspect the flashing.

What your roofer did is a traditional, time-tested method. If he was competent, you're fine. Don't try to fix something that isn't broken.

I understand completely with two caveats. the snow/ice break is something I'm unfamiliar 28th... the types of flashing I get. the house was built do that the rain just needed the siding meeting the brick to be water tight originally. The siding over time for whatever reason went bad and could not be noticed because it was behind the joist. I refrain from calling it a ledger board because it's not attached to the house on that side, maybe that's a technical error, but country code and most contractors won't use flashing unless the ledger board is actually bolted/attached to house. Here is runs parallel, but very close, too close perhaps for a siding contractor to fix the siding or install flashing before the joist (parallel to the house) level -I'm not sure. I agree with you regardless of code etc, the siding should be fixed and flashing installed, and the wood possibly wrapped where flashing overlaps, even though unfortunately it's not on the rest of the deck. Too much knowledge gained, too much trust falsely given up front, now too late into the contract as deck is near competition and details such as deck wrapping, type of fasteners, etc were not specified. Yet how much, if any in your opinion, can be accomplish without moving the joist running parallel to the house? One contractor who called regarding the situation, said although he can't say much until he sees it, says it may be possible to cut the siding and install flashing above the joist level and run it over the deck (I believe he means over the joist, which sounds like a very bad idea because that seems as it would create wood rot under the deck boards). Truly the only solution that makes sense z flashing with replaced siding such that water runs down avoiding windows, door, etc below. But is that possible without removing the joist? I would ask a siding contractor directly today but Sundays no one is doing business and secondly there are some very smart people on this sight that I have learned from in the the past. Your help included. HP (Learning in Northern Virginia and likely rest of country too many contractors are not worth their salt and it's extremely hard to find the good ones who don't overcharge.)