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Default Roofing questions, replacing old flashing where wood siding meetsroof, etc.

Hi all. Our complex is in need of some new roofs. Most, if not all, of the old flashing was nailed to the sides of the buildings, and not to the roof decks. My understanding is there is a way to cut off the bottom 6 inches of existing wood siding (to avoid having to remove all siding) and then, after the roofing work is done (which includes both ice and water shield as well as new flashing) they would replace the bottom 6 inches of siding with a trim board that is removable because it is attached with screws. I have a few questions.

1) what is the proper method of attaching the trim board to the bottom of the side of building? What exactly is the trim board screwed to, and what prevents water from getting behind the gap where the trim board meets the wood siding above it? I'd like to know the correct terminology so it can be mentioned when requesting bids.

2) Can the method of cutting off the bottom 6 inches of wood siding and replacing with a trim board (I'll refer to this from now on as trim board method) be used in all areas where roof meets siding? (e.g. areas that involve step flashing where side of roof deck meets side of building. and also areas like fronts and backs of buildings that involve continuous flashing at tops of roofs that meet siding )??

3) Can that trim board method be used around the bottoms and sides of chimneys that have wood siding as well

4) If the side of a roof meets side of building (step-flashing is involved) and there is horizontal siding involved, is it really possible to cut off bottom 6 inches and replace with trim board or does the siding have to be removed and replaced. (I'm asking this because it would seem awkward to try and cut off the bottom of horizontal wood siding at an angle, as opposed to the bottom of vertical wood siding in this situations)

5) Will the "trim board method" look lousy in the fronts of buildings, or look acceptable?

6) How many inches of ice and water shield should we require be installed from bottom of roof near gutter upward. Should we require 3 feet, or 6 feet?

7) We plan on requiring 6 inches of ice and water where siding meets roof. Should we require this only for sides where step flashing is involved, or also require this at tops of roofs that meet fronts/backs of buildings, where continuous flashing is involved?

8) We plan on requiring a drip edge where roof meets gutter. I assume a drip edge is nailed to the fascia above gutter, and tucked underneath bottom shingles. If that's the case, is it important that the nail heads be sealed with caulk, and should they also caulk the top of the drip edge where it meets the tar paper underneath the shingles so that, in an ice-damming situation, the water won't get underneath the top of the drip edge, and then the water could freeze, and force it to come loose, etc?

9) what is required at sides of roof on gable ends to prevent rake boards from rotting or water getting behind siding, etc? Ice and water shield? Anything other special flashing? What is the correct terminology?

Thanks.

J
 
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