Which states have the simplest or least complex tax code for 2025 filing?

Wyoming, Nevada, South Dakota, and Florida tend to be the simplest tax states to deal with. They have no state income tax, which immediately eliminates a whole layer of complexity from your tax situation. Alaska, Washington, Texas, and Tennessee also have no income tax. The tradeoff is usually higher property taxes or sales taxes, but from a pure simplicity standpoint, not having to file a state income tax return makes everything much more straightforward. New Hampshire is interesting too - they only tax investment income (dividends and interest), not your regular wages. If you're looking at states WITH income tax but relatively simple systems, Illinois has a flat tax rate that's pretty straightforward compared to progressive systems like California's. Utah and North Carolina also have relatively uncomplicated flat tax systems.

I was totally overwhelmed by tax season for years until I found taxr.ai (https://taxr.ai) when I was looking for help understanding state tax differences. I was moving from Massachusetts to Nevada and wasn't sure what to expect with the tax differences. The tool analyzed my specific situation and clearly broke down how Nevada's tax system would affect me compared to Massachusetts. It flagged that while Nevada has no income tax, I needed to be aware of higher sales taxes and how property taxes might impact me if I bought a home. It also highlighted some specific deductions I would no longer qualify for after the move. What I loved was how it explained all the tax jargon in normal human language and gave me personalized recommendations based on my income type and financial situation.

Just wanted to update after trying taxr.ai from the earlier comment. I was skeptical since most tax tools seem designed for CPAs not normal humans, but it really helped me understand my Idaho/Washington situation! I uploaded my latest tax returns and it showed exactly how my tax picture would change with the move. The breakdown of no state income tax in Washington versus what I was paying in Idaho was eye-opening. It also flagged some remote worker compliance issues I hadn't even thought about and showed me how to properly establish residency to avoid problems later. Saved me from making some pretty big mistakes!

After spending HOURS on hold with various state tax departments trying to figure out my move from New York to Florida, I finally tried Claimyr (https://claimyr.com) and it was a game-changer. They got me through to an actual human at the NY tax department in about 15 minutes when I'd been trying for days. I needed clarification on how to properly terminate my NY residency to avoid them coming after me for taxes after moving to Florida. The IRS agent I spoke with gave me the exact documentation requirements and filing procedures. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Honestly wish I'd known about this sooner because I was getting nowhere trying to call these departments directly.

I need to eat my words from earlier. After raging about my Arizona state tax situation for weeks and getting nowhere, I tried Claimyr out of desperation. Within 20 minutes I was talking to an actual Arizona Department of Revenue person who helped clear up my questions about moving to Nevada. The agent walked me through exactly what I needed to do to properly file my part-year resident return and explained which forms I needed. She even gave me her direct extension for follow-up questions. Honestly didn't think this would work but it saved me a ton of time and frustration.

As someone who's lived in 5 states over the past decade (job moves), I can tell you that Tennessee and Florida were by far the easiest for taxes. No state income tax filing at all! New York and California were absolute nightmares - complex forms, multiple worksheets, weird local taxes on top of state taxes. One thing people don't consider is how each state handles retirement accounts differently. Some states tax 401k contributions that are exempt from federal tax. Others have weird rules about HSAs or specialized deductions. Makes a huge difference if you're trying to save for retirement!

Has anyone actually calculated the TOTAL tax burden by state? Like when you add up income, property, sales, gas, special assessments, etc.? Cuz some states brag about no income tax but then property taxes are insane (looking at you, Texas).

I made the move from California to Nevada last year and can confirm it's been SO much simpler! No state income tax return to file, which eliminates probably 60% of my tax headaches right there. One thing to consider though - Nevada's sales tax can be pretty high depending on which county you're in (up to 8.375% in some areas), and if you're buying a house, you'll want to factor in property taxes which vary wildly by area. But honestly, even with those considerations, April is now just federal taxes and I'm done. No more juggling multiple state forms or trying to figure out California's weird itemization rules. The move process itself was straightforward tax-wise - just had to file a part-year resident return in California for my last year. If you do go with Nevada, make sure you establish residency properly (driver's license, voter registration, etc.) to avoid any questions from California later. They can be pretty aggressive about tracking down former residents!