Some have half of the roof in one color shingle, the other half in another color.

Yes, an asphalt shingle roof will eventually wear out, but expensive roof repairs generally stem from not replacing the occasional shingle blow-off or failing to put $5 of roof sealant at flashing areas.

When the shingles blow off the roof, I fix it.

If you decide to go with shingles - there is a company called SRS INC. just outside of downtown on the west side.

Prime and paint 3 bedrooms, $450.Remove texture from bedroom ceiling, skim coat, prime and paint, $250.Tear off old roof shingles and load into dump trailer, $600.Install walkway of paver bricks, $350.Pressure wash non-brick parts of exterior, $300.Etc, etc.So, after maybe five months, we had paid her about $11,000, and she went back home.Can/should I file as a "real estate professional"?

New shingles 2015.

So all but that one window is installed.The main roof, which is asphalt shingles, got installed.

Are the shingles curling?  

I began doing construction early on and fell in love with the process of seeing a house take form, from foundation to shingles.

.#3 Contact Local Contractors for 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.