The OP has an Annual Neighborhood Walk Survey to insure that our homes don't deteriorate. The impetus for this likely came in the 70's when there was an overall fear that Chicago would swallow up all of it's neighboring communities and that we'd end up looking like (and having the crime statistics of) our neighbor to the east, Austin.
Unlike some Gestapo communities where they dictate landscaping, fence height, house color and style, this little check in the system is pretty harmless. It is slightly unfortunate though. It means that as a homeowner you may end up sinking money into "appearance" related items that might not seem pressing as opposed to spending money on items that might matter - like new storm windows, insulation, safer electrical systems, efficient mechanical system, etc.
This year we were in violation for the soffits on our garage. I admit - they are a complete mess and need replacing. I'll also admit that I've been procrastinating on fixing out garage since we got the place. Overall, the structure is fine but the cladding is a mess. The terrible choice in siding and paint colors aside, there is no proper drip edge, various types of siding at each height, deteriorating soffts, etc. The base of vinyl siding definitely goes in the "what the hell were they thinking" department.
I purchased enough wood to replace all of the deteriorated soffit and will be doing a remove and re-locate job on the siding to at least get the siding on the alley side to look all the same (for our Neighborhood Walk Survey). I'll also be putting in a drip edge. I am priming all sides of the wood with a couple coats of oil-based primer and will be painting it all once it is in place. I hope to paint the entire garage with our new house colors this fall. It was another spectacular day in Chicagoland so I set up shop in the back yard and got to work. I'll begin installation next week.