Extra drywall goes to the trash other than maybe a small 2x2 patch piece; it warps, takes up a lot of space and costs $15 for a whole new sheet. 

then we'll need to find a roofer to patch the two resulting holes.   

I believe this was a known issue because my tenant and neighbor both said that before I bought the house, the seller was always patching up the roof.

He seems particularly concerned about having to fix things I implement (patching, repainting etc.) before selling when that time comes down the line. 

I recommend spending a little more for qualified contractors (especially if 203k) and trying to get the construction done quickly so you have some place to live without all of the heartache and holding costs.Kensington may be "up and coming" with good real estate values, but it will be more of a long term game, as the neighborhood is still quite rough in patches - especially on the outskirts.

Included patching,prepping small holes in drywall, all trim,doors.

Repainted all units, updated paint on exterior patches, built a brickwall with neighbor.

Second, tenants drilled holes in living room ceiling to hang their TV screen, I have to get a painter to patch that up is that deduction?

The people that make it past this rough patch, in the beginning, are usually able to turn this into their full-time gig.

But how do I know that it was a really good patch job and water will start leaking in a year?