Are there any tax estimators that handle self-employment income and complex state tax support?

Yes — there are tax estimators that can handle self-employment income and state taxes, though “complex state tax support” varies a lot by product.

Good options to look at

• TurboTax TaxCaster / TurboTax Full Service
  • Supports self-employment income reasonably well
  • Stronger for estimating federal + many state taxes
• H&R Block Tax Calculator
  • Can handle self-employment and state estimates
  • Often good for more common state-tax scenarios
• TaxSlayer / TaxAct estimators
  • Usually support self-employment and state returns
  • Less polished, but can be useful if your situation is straightforward
• FreeTaxUSA estimator
  • Good for federal and state estimation at a lower cost
  • Better for simple-to-moderate situations
• Customizable tax calculators or spreadsheets
  • Best if you have:
    • multi-state income
    • state-specific deductions/credits
    • S-corp/LLC/partnership income
    • estimated tax payments across jurisdictions

Important limitation

Most “tax estimators” are designed for:

• W-2 + basic 1099 income
• one home state
• standard deductions

They often struggle with:

• multiple states
• nonresident/part-year returns
• state-specific self-employment rules
• business deductions by entity type
• local taxes like city or county income taxes

If you have complex state tax needs

You may want:

1. A professional tax prep platform rather than a simple estimator
2. A state-specific calculator
3. A tax pro if you have:
   • income in more than one state
   • nexus issues
   • owners in multiple states
   • pass-through business income
   • credits for taxes paid to other states

If you want, I can recommend the best estimator based on your situation — for example:

• single state vs multiple states
• sole proprietor vs LLC/S-corp
• W-2 + 1099 mix
• states involved