Is this a single family home that could be used even just in part as a store, service, eating place, office etc..?

I would say a quote for the larger items and time & materials for the others. 

That will also inform what finishes you have to have in place, and items you need to upgrade to be competitive in the market. 

When I want something completed in a hurry I get permits and as much of the materials as reasonable stored nearby and make sure of contractor schedules, and don't rely on people you have not used before.

The only thing I can see is if you pay itemize your deductions and have an enormous amount of home mortgage interest on your current home.I used to manage a tax office but I'm no CPA.

Do you know what items are the issue?

I actually had about 10 items that I wanted fixed in my first property after the inspection.

If you had already the experience of a few flips and knew the type of items that always seem to pop up, I would think you would be in a better position to succeed.If you do proceed, be sure of your ARV (do not rely on Zillow or Redfin), your rehab costs (include some margin), your holding costs, and your selling costs (are you going to stage?). 

We trust his opinion and we haven't been let down yet, although we've overpaid on some items. 

If your other income is higher than $150,000, then none of your losses are deductible in the current year unless you qualify as a Real Estate Professional (addressed in item 6 below).5.