I had already addressed the water problem created by a gutter dumping under a deck, and water pooling in low spots.  

The only way to remove this from the wall is to use a diamond blade grinder and cut into this and score horizontal, vertical and diagonal lines and slowly carefully pry or chisel it out piece by piece trying not to damage the adjacent tiles. 

The builder then pulls down the plumbing, electrical and wall in the massive decks and turns these into illegal rentable suits.

I was at first frustrated that a wife asked me what color I was going to stain the deck.

The stair faces the yard, and it's not within 6' of an adjacent property.I found the code section.CHICAGO CODES 13-200-260 Porches and Decks Existing porches and decks may be repaired or replaced in the same location with construction of the same type as that of the existing porch or deck. (1) Existing porches not exceeding three stories in height may be extended up one story to the roof level regardless of their location with respect to the lot line or other buildings on the same lot, if in conformance with the Zoning Ordinance. (2) Existing porches may be enclosed, regardless of their location with respect to the lot line or other buildings on the same lot, if construction requirements of Chapter 13-60 are met.

A 3 bedroom 2 bath home has only one hvac system, one water heater, one garage door, 2 exterior doors, and no wood deck that will rot every 7-10 years.  

Once you receive an approved building permit, and at the last minute decide you want to extend the porch a foot out, or add a covered deck, what would the typical process to do so be?

As the area continues to turn around I plan on gradually making larger improvements, most notably washers/dryers in each unit and roof decks the units.

We also built a rear deck and roof deck.

interior/exterior upgrades (granite, deck, sunroom)?