What brought you to 30A and are you practicing architecture/development there?

I will say this gentleman has mentored me through purchasing the property, demolition, pulling permits, architecture, and other aspects so far.

In Portugal we have many clients which buy the plot, develop Architecture project and submit in Municipality to approve.We develop 3D real images and sell.Construction take around 9 to 12 months, and usually final client get better price than ready house to move in.The demand it’s so high, this kind of projects, when have good location, stay only few weeks in market.But our reality can be different of other countries. 

Yes having peaks and valleys adds to the cost so when considering to purchase a home I always take into consideration the steepness of the roof and the architectural design.

The two primary differences are the quality of construction and the architecture.

And it will look Architecturally like a low scale house.Not an improvement in curb appeal (IMO).Some streets have a lot of this, some have not so much, some have none.Another low scale alteration is to take building grade lumber and nailing up a stoop and steps with a railing and then just let it weather and rot vs building a proper porch.Personally I like the look of the porch that the house was designed to have, vs making it an enclosed vestibule.I didn't address the value question, because that might be more of a local Realtors opinion thing...maybe 3 or 4 of them.Just my 2 cents.

Hello Kendall,  Many years back I was in architectural sales myself and I left as the employers wanted to play games with commissions and I lost about 56K on one that owed me that.

I mainly need gated security and patrols,  a reliable water source, Maintenance of common area landscaping, architectural control / guidelines, and trash pickup.

In addition to your full architectural plans/permits you to need obtain a separate permit from CDOT (Chicago Dept of Transportation) to cut open the street and your plumber will need yet another separate permit from the Water Dept.

I would recommend while under contract and getting the loan, pay upfront for the architectural plans and get it submitted to the City as soon as practical.