Would a custom trim contractor be able to knock this out?

You can only allocate a couple % for this - the other regularly recurring expenses like roto rooting, regular tree trimming, asphalt sealing, etc can all be allocated as part of your diligence and be pretty firm year over year.

@Christopher TellesYou are looking at about $5,000 per bathroom which would include labor and materials (demo of the old bath, new tub, new diverter and trim kit, new vanity with granite or cultured marble top, new sink faucet, new toilet, new tile surround, new tile floor, and lastly a towel / shower rod).

The painting will start with the trim tomorrow and go from there.We also have one of our in-house guys connecting the heat up to the 2nd floor.

If it's grown over with weeds, trim it up and throw some weed killer on it and make it the tenants responsibility.

If you ever need any trim carpentry help feel free to contact me.

Immediately I’ll paint the outside white with black trim at the suggestion of @jessraden.

I like SW pro classic trim paint in latex and really like bm advance but it is a little pita to work with and clean up but dries flat and hard though.

Renovations consisted of all new paint, flooring throughout the house, trim, lighting/ceiling fans, and fixing many small issues as they came up.

Installed all new doors and baseboards and trim.