Not only do the architectural shingles look better, they sit heavier on the roof and are harder for storms to tear off. 

Also, could try finding a bunch of architecture and construction management students to see if they're interested in a summer project for their portfolio.

Permits and architectural drawings are not free and not cheap.

If your not doing major renovation, Id recommend calling the building department and asking if you need stamped architectural plans.

I have been a licensed General Building contractor for many years as well as being an architectural designer.

The footing, lally column and anchor bolt issue is more of a structural design than architectural.

I plan to, ASAP, buy a condo for myself next to work, but mostly stay with my parents and Airbnb host the condo.I'm in love with a $200K studio on the Chicago River (Marina City, architectural icon, amazing layout, low HOA fees).

X number of parking spaces, X amount of space for emergency vehicles etc2) Get multiple bids and walkthroughs by architecture/engineering firms to get a few plans made up3) Get multiple bids by General Contractors to see how to execute agreed upon plan4) Use GC and architecture bids to secure financing5) ExecuteI know I am missing a lot of the specifics, but for now I am curious as to how to just do some napkin planning, so say I am looking at that 30,000 sq ft building, how many units would that fit?

There is not a distinction between a single family home (which could be in HOA) and a townhome (which could have no HOA) other than architectural/type of construction 

Additionally the approval of your architectural drawings (required for full renos and for raising ceilings) and the issuance of your permits will take some time here in Newark.