Definitely make those assessments during inspection or prior to making an offer if you can to save yourself the time. 

The “Big deals” are…You have to buy something you don’t already own, not pay off debt, renovate a home you own, or build on land you already own.You have to spend all the “cash” you receive.You have spend more than your net selling price.You can never receive or have control of the cash, you need a QI PRIOR to selling. 

@Andy LanyiGood comments on how to reduce tax bill. 

Refinancing  immediately prior to a sale - yes that is a cause for some seasoning. 

Do that every 2+ years, sell tax free, repeat, and you can be set for life ("live in flips"). 

According to the City of Chicago tax code, it costs $5.25 per $500 of the transfer price.

If you are not familiar with Scott, Scott was the Executive Director of the Opportunity and Revitalization Council, which was tasked in part to support and advance Opportunity Zone tax credits during the first Trump Administration.

I shifted from investing with a cash flow focus to the appreciation and tax benefits side of things.

Moving out of a state with income tax to a state without before selling, saving 10% or more in taxes. 

Working with a CPA can help you navigate tax implications, and staying focused on long-term planning will set you up for success.