Home and detached garage needs new roofs - advice?

Hi, I’m a homeowner and my insurance company has given me a starter check ($10,000 will be given for the complete job) for new roofs for my home and detached garage that’s downtown, hail damage and old age. I’m doing research on roofing and roofer options.
I’m looking for any tips or advice and have some questions below that come to mind.

My insurance agent said they may have underestimated the size of the house roof because she couldn’t walk it all, too step and also said code may require more expensive roofing (modified bitumen) on the garage than what she estimated. My insurance allows me 1 year to reroof.
My neighbor knows a roofer that she says did her roof and she highly recommends them.
I guess I’ll check with the BBB and also get a few estimates before I choose a roofer.

I know to require the old roof to come off as there are spots where an old roof is under the existing one and the current house roof was a poor installation where some of the shingles were stapled, not nailed etc.
I know to require nails instead of staples. I’ve been to consumer reports and they found roof price does not dictate quality in their tests. They highly recommend laminated shingles Owens Corning Oakridge or CertainTeed Landmark for their low price and long wear and strength.
They did not discuss flat roofs though.

I’m guessing the insurance company probably underestimated the costs and hopefully the roofer can work with them to get more money. I guess I may have to pay some of it myself for the level of roofing job I want.

General Q’s

  1. How should I choose/what should I look for in selecting a roofer and what precautions should be followed?

My home:
Is circa 1900, 2 story, the upstairs has some dormer windows, it’s the 3 tab asphalt shingles, about 2500 square feet size home. The roof is very steep.
The chimneys need repointing and are missing some bricks that I have. There is a evaporative cooler. The gutters are garbage, need replacing. I believe the roof under decking is all good, it’s 3/4 inch solid wood and the gapping is 1/4 inch and less.

Home Q’s

  1. Insulation on the roof, is there a radiant heat barrier that should be installed under the roofing?
  2. Is there a better way to channel the roof valleys and ridges I should insist on?
  3. What’s the best roof color, I suppose a light color or silver or white, to reflect the sun and for longevity or does it matter much?
  4. Is there a better way of flashing the chimneys I should insist on?
  5. Is the roof underlayment gap of 1/4" and under a problem-too wide?
  6. Is there a roof coating that should be applied to the new roof to extend it’s life?
  7. Is there any underlayment sheeting I should insist on?
  8. Is there flashing on the roof edges I should insist on?
  9. Odd question. since the roof is so steep is there a product that can be installed inexpensively for safety at the roof edge that helps keep someone from sliding off the roof?

The garage:
The detached garage is a flat roof, with a slight pitch to the center so the water runs down the center out the back in the alley, there is no gutter. It’s basically the size of a 2 car garage, but it’s a single garage with a work shop area.
The roof is rolled asphalt and the walls are stucco, the ceiling joists are 8 inch, 16 inch on center and there is a large center beam. The exterior walls are taller than the flat roof, in an art deco fashion where the corners are the tallest (maybe 15" inches taller). The interior walls are unfinished.
Some of the roof sheet decking is bad and the exterior walls top may be too.

Garage Q’s

  1. Insulation, I really think thick insulation sheeting should be applied under the roofing, I’ve seen this done on a flat business roof, any tips?
  2. I want to be able to talk on the roof as a patio with the addition of stairs on the outside of the garage, what type of roofing is best considering price and longevity?
  3. Should I install a wood deck maybe with perimeter hand rails over the new roofing if using as a patio?
  4. Is there an exterior edge flashing I should insist on?
  5. Is there a roof coating that should be applied to the new roof to extend it’s life?
  6. Is there a better way to channel the roof valley I should insist on?
  7. Is there any underlayment sheeting I should insist on?

Thank-you for any advice.

Jim in Colorado Springs Colorado