I plan to have my GC patch it with concrete and then cover it with epoxy paint.

Would it be much easier to remove and patch up the sheetrock instead of wood siding?

But there was about a 2 sq. ft. patch of stucco that was breaking apart from the house.

I'm not exactly sure if they were doing a patch job or just did not know what to do.

The house is being extensively remodeled, contractors crawling on top of each other …we have painters in one room, cabinet guy finishing crown molding on those 42” cherry beauties, there is a deck guy shooting the heck out of nail gun outside, garage guys patching the siding, mortar guy patching and tuck-pointing the chimney in other words … scheduling mess, aka typical flip scenario ohh and there is a plumber who just pulled in hoping to replace the missing copper The guy walks to the basement and falls down the stairs (faulty railing).

I can even patch holes in plaster!

So if you replace the entire roof it is depreciated over a few years but if you repair something like a patch of shingles it is a deduction for that year.  

If you can't get the piece out, you can simple fold the top into the hole and patch over it. if you want to re-install the rail into the deck, you may have to have new holes core drilled into the concrete.

as you state going the PM route will have rough patch's no matter the city area etc..

You left a patch of dirt when you moved out.