(I also have a lot of free time) I have irrigation and landscape lighting experience and some carpentry and painting skills.

In the neighborhood, there is a huge variety......brown, burgundy, bright yellow, black,  blue, light teal, etc. 

Renovation estimate seems light; $3k to update several apartments and repoint parts of the exterior brick work?

I heard mention of large fees for minor issues like changing a light bulb.

I definitely think there is a case to be made ... when we bought ours we used recent local comps for the land value and then broke out as much of "everything else" as we could ... roads, mailboxes, fences, light posts, there is a storage shed on site ... each type of "improvement" will have a different depreciable life, but it should get the weighted average down which will help ... there is a good podcast episode on this topic done by @jeffersonlilly early on ... you should look that up and check it out ... good luck 

He works with his banker and they’re working with him in light of his entire financial situation.

No red lights, quiet streets, a ghost town of a downtown made up of a few dive bars and abandoned buildings.

NEW TILE BACKSPLASH, NEW OIL BRONZE RUB PLUMBING, HARDWARE, & LIGHTING PACKAGE, BATHS HAVE NEW GORGEOUS TILE SHOWER W/ STONE PEBBLES, NEW TOILETS, NEW FRAMED MIRRORS, NEW VANITY W/ GLAZED CAB.

NEW TILE BACKSPLASH, NEW OIL BRONZE RUB PLUMBING, HARDWARE, & LIGHTING PACKAGE, BATHS HAVE NEW GORGEOUS TILE SHOWER W/ STONE PEBBLES, NEW TOILETS, NEW FRAMED MIRRORS, NEW VANITY W/ GLAZED CAB.

Satin Nickel Hardware & Lighting Package.