If the building has a heritage designation, or you simply wish to preserve the elaborate external trim or dentil or internal mouldings, these things are time consuming and skill sets to restore them, uncommon. 

I painted, installed some new trim etc.. but so far I have had to have a plumber come by to fix leaks and the shower drain which ran about $400. 

I went inside and took some measurements and also a closer look at some of the repair… All of the trim needs repainted throughout the house and about 1" of wall above all of the trim needs to be textured and repainted.

Then 30% after that upon the start of drywall and upon the start of electrical trim out, the remaining 5% then is due upon the completion the contracted work and signed punch list.

.- paint- trim- very light demo + dumpster- trim, a little flooring fix, commonizing the look and harden it (bath fans, remove storm doors, put fake bottoms in sink cabinets, add a tub grid drain, etc)- spring will need some concrete.that's it.

Trim painting is extra and install caulking at the top of the trim board and wall, it makes look better and it is cheap to do. 

We don't use gray, as most of our properties have wood trim in light or dark wood tones.

Paint primer interior and begin trim carpentry.

We are trying to trim our budget where we can save more money for investments.

Then I would replace the siding and paint the trim (check the windows while you're at it).