I knew that the roof had some issues when I bought the house. Some were easy to see from the ground, others were pointed out by my inspector. The sheathing was too thin for the 24" span of the rafters, and in some places it wasn't nailed to the rafter at all, allowing for a sagging appearance and obvious squish when stepped on. Inside, the heat damage illustrated the poor ventilation.
So... quotes. And more quotes. Each one higher than the last... except for the one guy in a pickup truck who sent his teenager onto my roof (without appointment or permission) while I was in the middle of a conference call. He was the cheapest. And I didn't hire him.
I learned all about soffit vents and ridge vents and underlayment and more than I care to know about roofs. What I do know is that I have 6 feet of crazy thick coating around all the edges of my house to prevent ice dams from leaking through, and then other self-healing awesomeness over the whole house, and a ridge vent that's extra puffy, and a 50 year warranty. Yep, five-zero. 50.
New roof! I painted the shed door and trim to demonstrate the new color scheme... but I still need to get the eaves of the house painted.