My first inclination would be to do a little homework (due diligence) : Take a look at the other homes you mentioned that are similar to your home (maybe even with the same lay out and architecture but have the extra living space: if you can get into one of those and walk it) to assess the flow and space, that would be great! 

That's solid adviceI just need a sanity check to make sure this is worth pursuing, a valid pattern/architecture, and worth the squeeze.Since I get to create an entity structure from scratch I want to do it right and fully understand what I'm getting into.I might be over thinking this by planning for too much at once?

For example, you can convert “architectural beauty” of a set of 5 properties into numbers then rank them based on the difference in income they may generate due to this aspect.I would say that MATH is one or the most important language when it comes to REI, because if you do the math wrong or you do not know how to convert qualitative aspects of a given set of properties into math and rank them, it will cost you money.For most people maximizing return is the single most important thing.  

.), but given you are working in the same footprint of the existing building I wouldn't see that being an issue.You can figure most of the information out on your own, but I've always found it easier to find experts at what they do like @Prashanth Mahakali and @Samuel Pavlovcik so that you can lean on their architectural expertise.

I'm a student at Mizzou in Columbia, Missouri, completing my last year in the Architecture and interior design program.

I have yet to invest but my background is in architecture (9 years) and more recently a real estate agent (6 months). 

@Anna Laud, is this an architectural significant house?  

The most popular degrees I have seen for this career are: Economics, Marketing, Finance, Accounting, Civil Engineering, Urban Development, Architecture, Construction Management, Business Administration, Business Management (Please let me know if I missed other degrees).

Not clear on what your question is but if you're asking how to control the continuity of design aesthetics with multiple builders in the same communtiy then as the developer you would set the architectural design and review process.

Likely check in with Vera then, as I don't think an insurance claim would be worth it.Any strong opinions on 3-tab vs architectural shingles?