Tax Tips & Insights

The ProCFO Resource Library.

Educational tax content from Stephen Challinor, CPA. Built to keep you informed, not to replace a professional consultation. Tax laws change: always verify with your advisor.

Business

LLC vs. S Corp: Which Entity Structure Is Right for Your Chicagoland Business?

The entity you choose affects how much you pay in self-employment tax every year. Here is how to think through the decision with a 40-year CPA perspective.

By Stephen Challinor, CPA · April 2026

IRS & Compliance

Got a Letter from the IRS? Here Is What to Do First.

An IRS notice is not a judgment. It is a request. Here is how to read it correctly and why responding alone is one of the most expensive mistakes taxpayers make.

By Stephen Challinor, CPA · March 2026

Tax Planning

CPA vs. TurboTax: Why Software Is Not Enough for Complex Tax Situations

Software asks what you enter. A CPA asks what you do. For anyone with self-employment, investments, or rentals, the difference is real money every year.

By Stephen Challinor, CPA · February 2026

Disclaimer

Tax laws change frequently. Content on this blog is for educational purposes only and does not constitute professional tax advice for your specific situation. Always consult a qualified tax professional.

Speak With Stephen Directly →