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Why are so many things broken?!?

I'm not sure where to even begin here. Trying to build a new website for my brick and mortar store that has been operating using the SquareUp point of sale platform. We previously have been running a separate website via SquareSpace, for the last 5 years, with ecommerce functionality, but with a limited selection of our products compared to what is in our brick and mortar. 
EVERYTHING is going wrong with trying to get this website to the point we can launch. Lost pages, data not being saved, text disappearing. Importing and synching items and images from the SquareUp end not working AT ALL! I spent all of today taking new pictures of product on the POS end, using a brand-new ipad with high quality camera, and half of them aren't showing up with listings. Products we've listed as available are being hidden. And HOW ON EARTH IS THERE NO WAY TO SORT ITEMS BY CATEGORY IN YOUR ITEM LIBRARY AS YOU'RE TRYING TO EDIT?
The final straw is the absolute tangle of shipping options. No simple stream-lined way to offer shipping via just one provider, based on value and weight of the item. We sell goods that range from $5-$500, from enamel pins to duffels. The shipping functionality is utterly infuriating.
Frankly, this platform is a nightmare. I am not a newbie, I have built multiple business websites over the years, and have been utilizing ecommerce since 2010. I was drawn to this platform combo of SquareUp + Weebly due to the fact that we have over 700 products in our brick and mortar, thought it would be an easy way to synch and coordinate inventory between the physical and digital spaces, the email marketing capabilities that are built in, and now our retail storefront being shut down due to the pandemic, seemed like a quick way to get all our products available rather than a limited amount. The entire process has been nothing short of hellish. I'm not even sure I want to stick with this long enough to find out if the email marketing is worth it.

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I am sorry you are experiencing the misery of what it is like to try to run a business on weebly. 700 products is too many to try to manage using Weebly in my opinion. I have tried to manage over 100 and that was near impossible, the batch capabilities are subpar and as you have experienced every single interface works differently with products, there is no streamlined way to do anything. 

I am surprised that you decided to move from Squarespace. I have heard so many good things about them. I am part of a large private group of artists and someone recently asked who everyone was using for e-commerce and who was happy with their service. Out of hundreds of responses, the number one platform was Squarespace, the second was WordPress (although those seemed to all be "WordPress fanatics" if you know what I mean), third was Shopify and Weebly was by far last and most complained about the service. I am literally just here because my irritation has not yet reached critical mass, but I am already building a Squarespace site on the side.

Years ago when Square up bought out Weebly I was really hoping that there would be vast improvements to the platform. Next to nothing has changed since they purchased Weebly. The customer service here (chat) has been the worst I ever received from any service. The forums are really the only place to get help, unfortunately. 

I might be wrong, but you might find that the "email marketing" is not even included and you have to pay an upgraded monthly price to even reach your customer base. There is a lot of very ambiguous wording regarding their email campaigns. 

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