They did explain that the one STR per "building or property" means one per parcel and followed with examples: A multifamily, a house with a cottage, or a house with an in-law quarters will only be allowed 1 STR.

Additionally, the lot is splittable into 2, 3, OR a "cottage court", which allow up to 8 buildings on the property (this is all confirmed with the city and I consulted with a friend of mine who is an engineer and has drawn up several of these cottage courts and says its feasible). 

I want to change the property lines to make a small, very manageable 0.25 acre parcel that has the rental cottages on it, and then sell the 2.0 acre parcel.

sure seems to be hurting the Cheese makers ….

Are some of the buildings repeatable - ie cottages etc.

Concede the territory and take your money elsewhere.If you like the hassle free money these properties have been so far, you're not prepared for the intense (and losing) fight ahead of you.Your cheese is moving. 

Andrew, Illinois REIA has monthly meetings in Belleville and Cottage Hills.

These are all single unit cottages a total of 8 on the property.

Who Moved My Cheese - teaches how to deal with changes 3.

I grew up in that area and have great memories of our family renting a cottage on the beach in the summers.