They also want 3 layers of 5/8" drywall on all posts and beams.

My 1880s Chicago home doesn’t have a traditional sill plate but rather a 12x12 beam that sits on the foundation.

I'm pretty sure that the slab is not resting along on a brick wall and must have some sort of retaining wall or columns/beam system.  

Laser focused on Massachusetts properties, timing numbers, & networking 😄🙌

Like I said you have the work ethic, now just combine it with laser focus and you'll be unstoppable!

If zoning requires the home be “modular” or installed on site as opposed to transported on a permanently fixed I-beam than you will have to order it as a modular home in the style of MH Advantage.

Brush up on building code requirements: in basements you're looking for egress windows that are 5.7 sq feet or more openable (3ft by 3ft casement style windows work best), and ceiling heights 6ft 8 inches or greater (as little as 6 ft 4 inches is ok under ductwork and beams though)Sounds like your basement would be a home-run to generate some extra rental income - Happy to talk through the details of that strategy with you, just shoot me a DM! 

For one of my rental properties, I had a contractor do 2 repairs (small roof repair, replaced four windows) and 4 improvements (added support beams in crawlspace, added gutters and downspouts, added basement access door, added soffit).The work was completed in December 2020.

Brush up on building code requirements: in basements you're looking for egress windows that are 5.7 sq feet or more openable (3ft by 3ft casement style windows work best), and ceiling heights 6ft 8 inches or greater (as little as 6 ft 4 inches is ok under ductwork and beams though)2.

Its a building from the 1850s, and it looks like it will require all new siding, major masonry work and support beam replacement in the basement.