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Here is the 20 point roof inspection check list:

1. missing shingles, tiles, slates or nails?
2. cracked, curled or missing shingles?
3. lots of fine gravel-like granule in the gutters?
4. dark, bare spots on your roof?
5. water flowing properly through the drainage system?
6. cracked sheathing?
7. gutters securely fastened?
8. cracks or open seams in your gutters or downspouts?
9. cracks in the mortar and bricks on your chimney?
10. bricks missing in your chimney?
11. caulking missing around chimneys and vents?
12. signs of water damage at eaves and overhangs?
13. roof ridge appear straight?
14. roof surface appear to be flat without sags or dips?
15. flashing installed properly?
16. damaged or missing flashings?
17. damage to valley flashing material?
18. water pool in some areas of a flat roof?
19. rotted or warped wood shakes or shingles?
20. caulking used to seal flashing material damaged or missing?

Here are the 13 most possible spots you should take a look first:

Chimneys

Damaged or improperly installed flashings around chimneys causes the most leaks in homes. Even a hairline crack above the flashing can cause a serious water leak.

Loose Roofing Nails

A loose nail which has backed itself out of the roof sheathing can be the cause a roof leak.

Bare, Cracked or Missing Shingles

Water leaks can be caused by cracked or missing shingles. Sometimes missing gravel-like granules on your shingles, also known as bare spots, can also cause leaks. If they do not, they are a sure sign that they will in the near future.

Furnace Flashing

Furnace vents usually have a metal storm collar and if the collar becomes loose water leaks will occur.

Roof Valleys

Damaged metal flashing or rolled roofing can cause water leaks. Some builders simply lace the shingles together and failing to properly cut them causes water leaks at the roof valleys.

Plumbing Vent Flashings

Some plumbing vent flashing incorporate aluminum and rubber seals. Look for cracks in the rubber seal around the plumbing pipe. Some seals do not hold well to ultraviolet radiation and fail in about 10 years.

Head Wall Flashings

When the roof stops at a vertical wall, a head wall flashing is used to prevent water from leaking into the house. The flashing should extend over the shingles at least three inches and must bend and extend one inch into a mortar joint.

Wall Step Flashing

Step flashings are used where a roof climbs alongside a vertical wall. Look for rust or holes in these flashings.

Leaks Caused by Ice Dams

Ice dams can block the flow of the water down the roof and cause water leaks, especially at the edge of the roof. To prevent it from happening install ice dam membranes under your shingles.

Leaks Cause by Wind Blown Rain

You will see this type of water leak during rains coupled with heavy winds. To prevent it from happening install tar paper and ice dam membranes under your shingles.

Cracked chimney bricks

Chimney bricks can develop cracks and cause water leaks inside your fireplace.

Missing or cracked siding above roof

This will cause water to enter behind head flashings and then into your home.

Water Damaged Caused by Water
Condensation in Attic

Improper attic ventilation causes water condensation in your attic and over time leads to major damage to your roof and attic insulation if not addressed.