OK.
The problems that I see just from the photos...
Photo 100-225
1. It looks like the oil tank is getting ready to fall off its supports. The oil tank looks OK, but I'd be very worried about its condition where it's up against the brick. Figure at least a couple hundred to put it on the proper legs.
2. The chimney looks like it could have serious problems.
Photo 100-226
3. Those rust stains on the siding are likely just the tip of the iceberg when it comes to roof leakage. Don't be surprised if there are serious structural issues.
4. Windows are definitely dated.
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5. You're not kidding that roof has issues. Another good heavy snow and it might have even more issues.
6. Looks like the bottom of the door frame is rotted from water splashing off the step.
7. It may be an optical illusion, but the house may be sagging a little on the left side towards the door.
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8. Garage needs paint and a roof, but other than that, it doesn't look half bad.
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9. Neighbors are too damned close.
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10. Uhm... Yeah. That speaks for itself. Roof is gone, chimney has one brick in the grave, another on a banana peel. It looks as if it has been patched several times. It may require a complete tear down. It also looks as if it might be sagging away from the house near the roof.
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11. Nothing too out of the ordinary in that photo, except for the color. Uhm... What is that wire wrapping around the siding and boring through the wall?
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12. Retract that on the garage. It's pretty evident that that wall is starting to collapse. Probably a rotted sill. If you want to save it, you'll have to jack that wall up, dig out all of the rot, rebuild the sill, and then correct the water problems that led to the rot.
Obviously it's going to have a well and a septic system. You'll have to have those inspected.
Things to have the property inspect for, as well.
1. Condition of wiring, especially in the ceilings where the roof is bad.
2. Any insect infiltration around the sills.
3. Condition of interior plumbing.
4. Condition of heating system. If the crawl space has water in it, that makes me believe that the boiler or furnace may be in serious trouble.
Things you want to look for as you tour the interior.
1. Doors that won't close straight.
2. Windows that refuse to open (unless painted shut).
3. Indications of sagging floors.
4. Any evidence of rodent or insect infestation.
It could be a nice little property, but it really looks as if you're going to be spending quite a bit of money fixing it up.