Alright, I'm a rookie and haven't done this before. Aside from the other issues of a 107-year old house, it seems that the installation of our roof (3 years old and seems quite solid) is tainted by the installation of the rain gutters. In some places, the gutter is pushing back the bottom layer of roofing material (sorry I don't know the terms). In some cases, this is causing (or allowing) water to run BEHIND the gutter and the house. I'm curious whether roofs ALWAYS have some sort of flashing joining the gutter and the roof, or only when they don't meet correctly. There are also spots where the roof curves back up just slightly before reaching the gutter causing water to puddle a bit. I'm just assuming I should fix this and looking for confirmation.