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Confused about Tax Collection Situation

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I'm pretty bewildered at the convoluted sales tax-collecting process on the Squarespace platform. 
I have a Commerce Squarespace Plan and it's connected to my taxer account but I just discovered, after numerous sales, that I'm not collecting any sales tax from customers...

Why isn't the 'automatic' tax collecting process automatic? Is there another platform where it is automatic? Why isn't there a simple, straightforward, honest way for business people who aren't web developers or internet savvy people to simply create their website and store and have things run smoothly? I need a product for an idiot.

From what I understand, I have to go into TaxJar and set up the sales tax collection manually...which isn't at all 'automatic'. I also have to be register in every state I intend to sell products to? Why? Aren't I just paying my sales tax to my state at the end of the year, or do I have to report separately to every state from which a customer buys? I don't get it..

The whole reason I'm paying the extra money for a commerce plan is to make the tax collecting process easier...and it doesn't seem to be working. So Squarespace is gladly reaching into my pocket and taking a few hundred more out of my pocket while I'm not even buying what I thought I was. ..Not a great way to do business or keep clients.

I've searched the forums and it looks like there are plenty other irritated and confused users of the Squarespace platform. If anybody has any advice, either on how to deal with the issue and simply collect the appropriate tax from customers at checkout, or for a better platform that is more idiot-proof and intuitive, I'd be most thankful for your input!

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