Utilities.Tenant agrees to pay for all utilities connected to the property such as sewer, cable, television, telephone, water, steam, gas, waste, trash, or electricity.

-Their street engine product is also great, if you are actually "driving for dollars".

Since most of the homes that flooded took on electrical damage, you will almost certainly need to file a permit to do renovation as you will need the electric company to shut the power off, provide temporary meters, and turn the power back on.

I am looking for insights from anyone who has recently upgraded their electric service in Chicago.

To me, these are no different than college degrees (and some cost as much or more): you wouldn't major in engineering if you wanted to be a marine biologist.  

What I do for my units with shared meters is I charge 50% flat to each tenant which prevents waste I get no issues with any waste due to this but the ones that share electric bills do get many complaints due to the size of the bill.

Here are a few Walmart deals that I found that could be useful$15 - Chefman Rapid Boil 1.2L Electric Tea Kettle - https://www.walmart.com/ip/Chefman-Rapid-Boil-Glass-Kettle-1...We have this kettle and it has been solid for 2 years now.

I am getting a lumpsum estimate for things like electrical, plumbing, but I am not sure what the cost is for. 

Everything else will follow, reverse engineer, and get started. 

You mentioned a career change, I think going into the trades like plumbing and electrical are great and you can make good money doing those, but I think you may be taking on too much by trying to do that right now.