Carolina so prices im sure are different, but for a 30+ year architectural shingle on a house that size I would figure it would be closer to 4,500-6k (for a licensed roofing contractor). 

If I company  shingles my personal house do I have to request the info as well?  

https://www.oneprojectcloser.com/how-to-level-a-plywood-or-osb-subfloor-using-asphalt-shingles-construction-felt/

I took pictures of damage on all sides, cut and removed the tree limb, covered the hole with a little roofing felt and a couple of spare shingles (I drew with paint "Do not step" on the shingles), and tacked a piece of plastic over the hole in the drywall.

You used to be able to do a roof over or new shingle roof by yourself, if it was under 500 sq. feet.

Say 220 was roofing ststems for expenses, 221 could be felt, 222, shingles, 223, hardware (nails, screws, trim, drip trim, vents, sofit) 224, decking/lumber, 225, roll roofing (including rubber systems) 226, glue/adhesives...you get the idea.If you are knocking out say 4 basic floor plans, different elevation but all the same materials/grades, you are buying bulk and allocating costs based on the plans per plan.

Looks like there's no flashing along the side and also needs some areas to be re-shingled.

What about roof maintenance (replacing a few shingles)?

The roof is less than a year old with I.R. shingles and most things here are new or good condition which IMO should keep cap ex low for me.  

It is not always the shingles that can be the issue.