Many FHA loans will require someone to address peeling foundation paint, trim, etc. 

Typical items I have charged good tenants for that they didnt notice until move out are large digs in wood floors, holes in walls from installing large add on shelves, part of appliance broke such as refrigerator or oven handles or shelf, removed curtain rods or installed rods removed leaving wood trim damage.

You need to put windows in and what are called jam extensions BEFORE trimming out your house.You trim out after you drywall but your drywall and window installations don't really depend on each otherHowever, you need to know if you are doing a pocket replacement or new construction windows as that will have a big impact on your order of operations. 

We just got done building a similiar spec house that we sold and it cost around $310k and we did all the work, Foundation, framed, sided, paint, trim, ect. took 8 months but i sold it for $525k.

As I continue to look at property listings, one thing that I always struggle with is establishing the fine line between "needs rehab" vs just stylistically different than my (and 'mainstream') tastes.For example, I see a lot of properties that are advertised as 'move-in ready' but the pictures show very outdated styles like oak cabinets, oak trim, brass fixtures, etc.

Now, I get to figure out who owns the land next to me, it is a vacant plot that is a small forest, to tell them I am trimming some of their trees.

Trim looks nice and everything.I don't mind getting a little dirty for now.

When I ask him to change things on the facade with pictures and examples from other projects, he doesn't really change much other than colors of the building and different trims and lips.  

Understanding of course that some of the answers will vary by region, I'm looking to average the answers, so to speak.1) How much do you spend per year (in dollars not percentages) for ongoing maintenance such as caulking, reglazing windows, replacing wind blown shingles, repairing loose siding or trim, loose door hinges, tightening loose railings, etc?

Trim the hedges every quarter and replace mulch every 1-2 years.