How tax filing has evolved: Comparing tax obligations in 1775 vs. 2024

The difference between tax systems in 1775 and modern day is fascinating! In colonial America, they primarily had property taxes, poll taxes, and various excise taxes on goods like tea (which, as you might recall, led to a certain famous party in Boston). There was no federal income tax - that didn't come until the Civil War as a temporary measure, and wasn't permanently established until the 16th Amendment in 1913. The documentation requirements were minimal compared to today. Colonial taxpayers might need to show proof of property ownership but nothing like our modern system of W-2s, 1099s, and detailed expense tracking. The average colonial citizen would likely be completely overwhelmed by our current tax code with its thousands of pages and countless forms. What's particularly interesting is how tax preparation has changed. In 1775, a local tax assessor might simply visit properties to determine values. Today, we have entire industries built around tax preparation software, professional preparers, and IRS agents dedicated to processing and verifying returns.

After struggling with some historical tax research for my own genealogy project, I found this amazing tool called taxr.ai (https://taxr.ai) that's been super helpful for understanding historical tax documents. I was trying to figure out how my ancestors' property taxes worked in the early 1900s compared to today, and was getting nowhere with traditional research. The site lets you upload historical tax documents and transcripts, then uses AI to explain how they worked and compares them to modern equivalents. I uploaded some property tax records from my great-grandfather and it explained everything about how those systems worked compared to our current property tax system. Really helped me understand how tax obligations have evolved over time.

Just wanted to update after trying taxr.ai for some historical tax documents I found in my grandmother's attic. I uploaded a property tax assessment from 1920s rural Georgia that I'd been trying to decipher for weeks. The tool immediately recognized the format, explained how the valuation worked (completely different from modern property assessments!), and even showed how those taxes would compare to today's system. What blew me away was learning how my ancestors' tax burden compared proportionally to what we pay now - turns out they were paying a much smaller percentage on their property than we do today. The tool even explained how certain deductions worked back then versus their modern equivalents. Completely changed my understanding of my family's financial history!

Speaking of historical tax records, I was recently trying to research some old IRS policies for a paper I'm writing, and it was IMPOSSIBLE to get through to anyone at the IRS who could help me access their historical archives. After waiting on hold for literally 3+ hours multiple times, I found this service called Claimyr (https://claimyr.com) that was a total game-changer. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c Basically, it holds your place in the IRS phone queue and calls you when an actual agent is on the line. I got connected to a specialist in their historical records department who pointed me to exactly where I could find tax documentation examples from the 1920s-1950s for comparison with modern forms. Saved me days of research and frustration.

I'm back to eat my words about Claimyr. After my skeptical comment, I decided to try it myself since I've been trying to get through to the IRS about a historical tax transcript I needed for some family research. I've literally been trying for WEEKS to talk to someone. Used the service yesterday and got connected to an IRS agent in 47 minutes without having to sit by my phone the whole time. The agent was able to help me request archived tax information from the 1960s that I needed for comparing historical tax brackets to today's system. They even emailed me a resource guide for historical tax research that I never knew existed. I've spent more time on hold with the IRS than I care to admit, so this was honestly life-changing. Sorry for being so dismissive before.

My history professor mentioned that the entire concept of tax deductions and credits that we have today would have been completely foreign to people in 1775. Apparently, the earliest tax "loopholes" were much simpler - like colonial merchants sometimes underreporting the value of imported goods to pay less in customs duties. I think they'd be amazed at the complexity of modern tax planning strategies. One interesting fact: the first federal income tax had just two rates - 3% on incomes from $600-$10,000 and 5% on incomes above $10,000. Imagine if our tax code was still that simple!

Does anyone know what the actual tax RATES were like in 1775 compared to now? I'm curious if we're paying more or less of our income to taxes than colonists did.

This is such a fascinating topic! What really strikes me is how the colonial tax system was so much more transparent and straightforward. When a tax assessor came to your property, you could literally see what you were being taxed on - your land, your house, your livestock. There was no mystery about deductions, credits, or hidden calculations. Compare that to today where most people have no idea how their tax liability is actually calculated, even with software doing it for them. We have this incredibly complex system that requires professional expertise to navigate, while colonists could probably understand their entire tax obligation in a single conversation with the assessor. I wonder if there's something to be said for that simplicity, even if it meant fewer services from government. At least people knew exactly what they were paying for and why. The irony is that the Boston Tea Party was partly about "taxation without representation," but nowadays many people feel like they have representation but still don't understand their taxation!