Hiw do I cover nail heads from last row of shingles? 

Shingle missing?

As with Apartment buildings, lead paint, knob & tube wiring, aluminum wiring, flat roofs, asbestos shingles, in ground oil tanks, etc. can all be issues.

The roofer wants to tear off existing roof (only 1 layer of shingles) and replace with 3 tab 60 mph rated shingles.

Roof is in decent shapeMy repair estimate = 20k----------------------------------------------------------------------------------------------------------------------House 4 : 2 bed 1ba, 1058 sq ftARV : 200kRepairs : Roof decent, a few of the shingles were coming off in the middle I don't know if thats a easy fix or not, new floors throughout, bath and kitchenMy repair estimate = 40k----------------------------------------------------------------------------------------------------------------------The houses were not in terrible condition they just all seem to be outdated, they were built between 1935 and 1950. 2 out of the 4 houses are currently being rented out.

Maybe consider the lower edge of the shingles higher in the gable.A new entry door sounds good, make sure it's architecturally correct (NOT Victorian with a big oval glass!!).

When the inspector came today, we FAILED INSPECTION because they already covered the sheathing with all the shingles.

Try this... build a much larger column base at the same height as the bottom of the stone, maybe tapered (bigger at the bottom) and made from a similar stone, with a much larger column (easily built onto the existing post) resting on top.Find a NATURAL, neutral-colored, plain stone or slate, and tile the raised concrete stoop.Paint the entry door a deep, very rich color that complements the brick.Then, the gable on the right with round-butt shingles (I think) needs a lighter color, maybe even a bit bright to complement both the brick and the entry door, since it extends over the stoop.Finally, taller greenery under the stone with a lower front level of varying texture and color (especially around the entry) will result in the stone being much less prominent.

Material will be $130/ square for shingle.

One contractor says he'll put on a new roof, 30 year dimensional shingles over existing roof for about $6000, using Tamco shingles (http://www.tamko.com/ProductDisplayTest/tabid/53/ControlType/productDisplay/itemid/168/Default.aspx) .