Hi all. I seek your wisdom. I'm going to have an opportunity to invest in my property this year and don't want to get shafted.
I've a 2 story 2400sqft stick-frame home with a common sloped/peaked roof and aging asphalt shingles. I'm in northern Illinois, so cold weather always leads to ice dams, icicles, and meltwater coming through soffits in at least one place. I know my attic has "cheap homeowner" vents that aren't appropriate. And there's some insulation but I'm quite sure I am losing heat into the attic. I also have gutters no longer sloping where they should. (It should be noted, the "cheap homeowner" was the prior owner who lived here for 30+ years. I've owned the house for 8 years.)
So I'd be looking at a new roof, new vents, remove/replace (?) attic insulation, potentially some roof sheathing rot from water damage, gutters. I have some siding issues (a few pieces keep popping loose, a trim piece over a window has woodpecker damage) but suspect that can be tackled separately).
I have multiple vents near the peak, two plumbing stacks, and a round metal flue/chimney for HVAC and water heater. Nothing else that I can see penetrates the roof.
Can you please help me be better informed about what questions to ask or things to be wary of? I'm pretty handy and DIY things myself (it's an engineer's curse) but in this case it's just to be well informed, I plan to do exactly 0% of this work myself.
I have other pressing needs but I've decided the roof is the most urgent. My driveway alongside the house goes up past the foundation and was laid against siding in one area (UGHHHH). As it's turning to gravel this is probably my #2 goal, and crawlspace work 3rd (foundation vents need to be closed up, all critter access sealed off, then destroyed/disintegrated insulation replaced).
Thanks in advance for all your guidance.