I always suggest that people look at the transfer tax form and rules to identify the transactions that are exempt from transfer taxes, and to then try to structure things to fit into an exemption where possible.

The $500K exemption might not be enough for a lot of people...

From PD Department of Revenue website:"Some real estate transfers are exempt from realty transfer tax, including certain transfers among family members, to governmental units, between religious organizations, to shareholders or partners and to or from nonprofit industrial development agencies.

There is also a short term gain (held property for < year), so the gain is also taxed at a rate that can range from 10 to 39% based on your tax bracket.Also, sometimes you will have a CPA tell you, if you were to stall the rehab or sale of the property and sell it just after the 12 month mark, that would exempt you from the SE tax, that is also wrong advise.

Social security, pensions, and retirement plans are exempt from garnishment. 

When the owner of a disregarded SMLLC, Sole, or partnership (each partner is a parent of the child) is the parent of an employee-child, the wages will be exempt from FICA taxes if the child is under 18 and exempt from FUTA tax if the child is under 21.Employing the owner's child in the owner's closely held business can be an effective tool to reduce the overall family tax burden.

Even with the $250K exemption, I will still profit $120,000.

Attached - screenshot of a public records request data return from 4 days ago - all taxpayer names (optionally exempt from website disclosure) for about 727,214 parcels... total cost?

Also, you’re correct that we have a Homeowners exemption in IL.

Or just gift it to the son and file a gift tax return, charging against lifetime limit (50/50 with spouse on gift, so that's 1/2 value against the $5.5 million each has in estate tax exemption).Or just gift the kid the income (but that doesn't get around paying taxes at his rate, in the first place).