Check your business insurance.
Start with the building department of the AHJ. Their application will tell you what you must have for the permit.
Who is going to create the plans? Whats necessary for the permit may not be sufficient for the building process (as you're starting out).
Sub contractors will make or break you.
Northern Illinois you'll need the bottom of the footing 42" deep minimum. For this and the concrete find really good subs.
Framing, with a helper you most probably can do it. You need accuracy, the more accurate the framing, the easier the rest of the job. Be mindful of where all the mechanicals go, make sure nothing structural is in the way of a mechanical necessity.
Exterior cladding can be a toss up, you may want to do the siding while subs work their trades. Brick work you may want to leave to others.
Roofing, in Illinois a roofer must be state licensed, find a good one.
Plumbing, again a state license, find a good one.
HVAC, may require local license, find a good one.
Electrical, may require local license, find a good one.
If you want to invest the time to learn you may be able to license for the above trades. Plumbing is hard to get the required hours for the test, the rest may not require field hours in your area.
Your subs work for you, but they also must work with you and each other. If you can find some who have worked together before that is a great benefit. Plumber should always be the first in by a day or two.
Spend as much time as you can looking at the bones of your own home and any you work on. If it looks right it most probably is. If it looks wrong figure out what looks wrong, decide if there was a better way.
Contracts at this dollar level are a must. Clear;y spell out what will be done and how payments will be made. Do not allow the client to dictate the terms, your the professional act as such. Do not allow the client to bring in their "cousin" to work on your project, never heard of that ending well.
Communicate well with the client, it will save a lot of misunderstanding and grief.
Tom