If they are only shingles and plywood, then you have a better problem.

That is for a single layer tear off and Ice guard and install a 30 year dimensional shingle.

If you're talking about a couple of missing shingles, that's nothing.

Does anyone have any quotes (materials+labor) for an asphalt shingle roof replacement for a two story 2200sf SFH in Indianapolis, Indiana ?

In looking at the roof (I'm not a roofing expert) I know it will need new shingles, but there is also some wood rotting that I is visible from the outside, so I am hesitant that the frame under the shingles are also compromised. 

If so, were permits pulled & were they installed by a professionalAre any of the homes rented to studentsIs there a flat roofare there asbestos shingles The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy .

HI Uday,I see a stucco crack by the door on the exterior (possible foundation issue) and possible rotted wood in one of the exposed walls, plus the shingles on the eaves looks wavy (rotted wood) and possible large ceiling leaks (more possible rotting of the roof), plus a lot more.Also electrical code might require you to update to modern code.It looks like a lot of unpredictable labor (possible cost over runs) and possible extended unpredictable hold time.You could get bids for everything that's wrong with it, if you understand what's wrong with it.The first step would be to get a home inspection and take it from there.Roof, foundation, electrical, etc....

Ask age of roof shingles/metal obviously. 

Hang your shingle and get to work!

If a big wind blows your shingles off the insurance pays for it.