I will be replacing the roof (has life, but shingle cuppage and moss have worn parts of it thin, into some layers of wood) new gutters needed as well.

Actually, what it had was new shingles; not a new roof.

Roof shingle or flat roof .No tile.On a 2250 sqft area living space .No garage no car ports .You looking at a total of .$168,880 .00Again please know this is. 4 month to 6 month project .

.#3 Contact Local Contractors for Labor Pricing / Hire a GC to ConsultCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.You can also pay a General Contractor a consulting fee of a couple of hundred dollars (per house) to walkthrough a few properties with you and provide a detailed estimate of prices that you can use as your 'menu for future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

.#3 Contact Local Contractors for Labor PricingCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

REgular HO policy should be 1600 to 1800 for a asphalt shingled, new build 2500 to 2000 squarefoot home.

On the two buildings I bought I installed new roof A/C units, new roofing shingles and I'm replacing some windows and adding ceiling fans.

Last cancellation notice was on a 32 year old CBS house not in a wind or flood zone with an almost new architectural shingle roof with secondary water barrier. 

One of my favorites recently is a roof with three layers deep of asphalt shingles that was still leaking. 

For instance,  a friend of a friend had tow truck experience, his employer was retiring and he wanted to hang his shingle.