My main contractor wants me to rip out and replace all the doors (8 of them) and surrounding trim, as well as take out the crown molding and baseboards which are very old, outdated and caked with layers of paint.

Over the years I've added a new AC unit, widened the driveway, had the trees trimmed , but have not had to do too much, to be honest.

Same with trim.

Basically none of the corners and trim are flush.

Basically, if you get a really big take off that is multi-stage, data management becomes really hard in Square... so I end up doing multiple iterations of the same job, one for trim, doors, and windows, another for lumber, another for siding, etc. 

Badly cut trim, bad paint, etc will not be as noticeable but those two areas will sell a house by themselves.

Remove door and trims.  

The objective of target date funds on the other hand is to periodically trim the asset allocation towards a more conservative stance.

inspections done, septic scoped, flushed, dye test, water/well tested; few issues, mostly minor, but for insurance reasons we’re asking owner to trim some trees back. 

(Though it's not the most heat reflective) I like Brown (from the mockup) architectural shingles.But throwing a few shingles of the chosen color up there before committing might be a good idea.In the mockup I put some trim around the windows and doors.Maybe toss some Pink Panther Insulation in the attic, add a roof vent or two, and make sure all of the windows and doors are sealed tight.And if you want Home Depot sells Rain Diverters, an L shaped aluminum strip to go on the roof above doors and AC Units.