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.

I think flipping is the way to go on this project since it’s my first deal which has always been the plan but very grateful for some guidance. 5 weeks of tear out, wall paper removal 🙃, new electrical, deck supports, HVAC install…we start putting it back together!

They're not connected to the electricity grid and don't have air conditioning or amenities.

Another consideration, @Jay Hinrichs, is whether the electrical infrastructure at the property can handle it. 

You may not occupy your apartment without electric service except during brief interruptions beyond your control.

If the house has the right updates for electrical it is a very in demand area for Section 8 tenants as well.

Here's what I've learned:Inspections Are Non-Negotiable: Always get a full inspection, but don’t stop there.Plumbing & Sewer: Have the plumbing and sewer systems checked specifically, as these are common problem areas in older homes.Electrical System: If the inspector flags any electrical concerns, bring in an electrician during the inspection phase for a detailed evaluation.

I did a lot of repairs myself but also hired a few skilled contractors for things like electrical work and plumbing.

There are exceptions - some properties are set up such that installing a few electric baseboard heaters might be possible to save on the gas bill - but i would still just shy away if not metered separately at the outset.  10) do shop for a lender and compare (usually pretty standard but there can be some fluctuation) - dont fall for the ones that sound too good to be true - there are gimmicks out there - big bank or reputable broker should do you fine.  

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