Damage limited to 1 K...I fully doubt it ,, any masonry repair is not cheap.  

Roofer #2 also does masonry and included $7000 to rip down several courses of brick along 2 46' parapets and rebuild them.

file_type=pdf&file_name=ESR-1385.pdf 3.2.2 Grout: The masonry units must be fully grouted with grout complying with Section 2103.12 of the IBC or Section R609.1.1 of the IRC, and having a minimum compressive strength as indicated in the tables at 28 days.

Still, that's a significant amount of water to be getting in your chimney with the masonry cap that's there.

It's a small 800 sq ft house but looks solid and it's made of masonry. 

I find myself still wanting to do this, but I would need someone full time that could fix things like the toilets, the walls, the masonry.

Make sure all railings/ gutters are secure, no crumbling masonry ect.You can also opt to add a personal umbrella if you are going to hold the property in your name for excess liability protection.GoodLuck!!!

Currently, I own a masonry business in Pennsylvania so I can write a lot about home improvement topics as well. 

Can anyone recommend a reliable and affordable contractor who specializes in tuckpointing and other masonry related work in the Chicago area?

For a three story building, you have to use masonry construction in Chicago.