Here is how the " rule of 5" would apply on a 45 degree roof with new plywood, architectural shingles, gutters, and tuck-pointing I have to replace.  

About $7k per SFH for me (tear-off, architectural shingles and a ridge vent).

The part that concerns me is the shingles with the caulked edge, if there is no step flashing under the caulk, you are almost guaranteed to have problems when the caulk releases, cracks typically within a few month to a few years depending on the sealant used. 

And no, those are not roof tiles by the way; they are decorative edge shingles instead of the standard trim.

So, let's say you have a roof with 20-year shingles that is 5 years old that was damaged in a hail storm and it needs to be replaced.

My roofer said flat costs more since materials differ from standard shingle.

Good schools, shopping etc are all close by.Ideally I'd like to use hard wood base trim at $1-2' cost from a supplier out of the area, the casing of course would be more, Masonite doors $70-80 ea, Schlage Door knobs, LP Smart Siding, basic roofing materials unless I could snag a good deal on class IV shingles - 5" concrete for the slab, Basic Vinyl windows.   

Get HD or Lowes to deliver the shingles roof top and put an add on CL and hope the guy you get doesn't fall off and get hurt.

It looks great and neutral and everyone likes it.For bedrooms each house gets the exact same carpet.For plumbing, each house gets PEX plumbing.If we replace roof or windows, each house gets the same brand of shingles or windows.Each house also gets the same plumbing and electric fixtures.These are things that we don't even try to contemplate.If it is neutral and goes great in one house, it goes in every house.

All kinds of issues...electrical outlets ungrounded, plumbing issues, flooring issues, a deck that was built wrong, a new master bath that didn't make any sense with a shower door hung wrong, a shower pan that had been nailed through, roof repairs made with 3/8" plywood, roof leak "fixed" by caulking the shingles.....new vent boot that wasn't nailed or seal, bath fan this venting into the ceiling....an unreal list.