Replacing a 3 tab shingle with a architectural shingle and ship lap wooden siding with more decorative and colorful fiber cement boards, I would think should be considered improvements.  

My name is Duncan Banks, I am a 30 year old military veteran with a BA and Master's in architecture.

I went to Clemson for school (both undergrad and grad in architecture) and then took a job in New Orleans for about a year and a half.

Pop the top might be a more aggressive strategy than I'd want to take on for my personal residence and first property in Chicago but layout changes are no problem at all, my background and current job is in architecture & development so I'm pretty comfortable with major changes as long as the bank account likes them of course.I really appreciate all of these thoughts on my current rentals as far as making them more systematic... really need to sit down and flowchart it like you just said, great idea!

I have a lot of respect for nice architecture and the feel of many art deco homes.

I studied Architecture in school, and always had a passion for real estate and architecture.

Here is a list of items to consider and most if not all of these items cost money:Land cost, zoning, city planning, due diligence items, civil engineering cost, architectural cost, marketing, attorney fees, construction cost and interest (carrying costs) on the loan.Don't get me wrong, there is a big reward at the end of the day if you do this right, and many people do.

Would this be something I should consult with an architectural firm or would a good roofing company suffice?

I have an architecture background (soon to be licensed California architect), I am interested in what is phrased as Architect as a Developer.  

I would be doing all pre-development research, architectural design and then building.