I don't know the rationale behind the receptacle orientation, but I'm sure that there's a story behind it.
At least we get to avoid the "ground up vs. ground down" debates here in the Windy City.
With regards to the EMT, depending on who you talk to, it's either because an overload in conduit doesn't present the same fire hazard as a length of Romex while its jacket is melting down as the result of an overload (the circuit breaker tripping isn't part of that story) or because it keeps unqualified people from doing their own electrical work (badly) and creating a fire hazard.
You also won't find a lot of PVC plumbing in Chicago, until very recently this was a cast-iron town that required poured lead and oakum joints for all of the main drains.
As to buying Romex at the big box stores, even when it was illegal to use in the whole County, they still carried it. One Department Manager told me that Corporate made those decisions without his input. He never sold a single foot of it amd had to explain his "poor performance" every month.
Romex is now recognized in Chicago, but you're not going to like the installation limitations.
"18-27-336.4. Uses Permitted.
Listed Type NM and NMC cable with listed fittings shall be permitted to be used only for limited extensions to knob-and-tube lighting or appliance branch-circuits in existing wood frame residential occupancies not exceeding three stories in height, but not where subject to mechanical injury as in new or remodeled building construction.
Type NM and NMC cable shall be permitted only in dry locations where concealed, in walls and floors of these occupancies."
Told 'ya you wouldn't like it...