What to tell me
The most useful thing you can send is a description of where the water shows up inside the house, when it happens, and what the weather was doing at the time. A stain that appears after a heavy rain from the east is a different problem from one that appears during a thaw after a week of snow. A photo of the ceiling and a photo of the roof from the yard, if you can take one safely, save a lot of guessing.
For carpentry work, tell me what you want the space to do. A porch that needs to hold a swing, a deck that needs to be stroller-friendly, a garage that needs to fit a truck with a rack on it. The details of the build come out of that.
What happens next
I will set a time to come look. On roofing calls I get on the roof and into the attic. On decks and porches I get underneath. On additions and kitchens I take measurements and look at the framing that I can see, and I tell you where I will need to open something up to see more.
You then get a written scope. It describes what I found, what I recommend, and what the options are if there is more than one. I keep it in plain language. If you want to compare it with another contractor's proposal, it is written so that you can.
If it is leaking tonight
Put a bucket under the drip and poke a small hole in the ceiling at the low point of the bulge so the water drains in one place instead of spreading across the drywall. Move anything valuable. If the leak is from an ice dam, do not go up on the roof with a hammer; that is how shingles get broken and people get hurt. Calcium chloride in a stocking laid across the dam will melt a channel through it until I can get there.
If the leak is from storm damage, a tarp is a reasonable stopgap, but only if someone can get it on safely. In high wind after a storm the tarp does more harm than good.
Where and when
I work in Springfield and the surrounding towns of Hampden County: Chicopee, West Springfield, Agawam, Longmeadow, East Longmeadow, Ludlow, and Wilbraham. Roofing runs from early spring until the snow shuts it down, with emergency repairs year-round. Interior carpentry, kitchens, and bathrooms fill the winter.
The best time to get a roof scoped is late summer and early fall, before the schedule fills with people who found their leak in the first snow.
A note on estimates
I do not quote from photos alone and I do not quote by the square over the phone. Every roof in this valley has its own history of patches, layers, and repairs, and the price of doing it properly depends on what is under the shingles. A written scope after a visit is the only number I will stand behind.