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Additional / upsell line items in shopping cart and penalty charges

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I'm just now considering which website builder to use while starting my new business.  I'm technical and can code but web development isn't my forte.

I'm starting a business for equipment rentals and I'd like to customize some of my shopping cart functions.

1) I'd like to recommend items to upsell to customers

2) I'd like to add an optional insurance line item

3) I'd like to make sure I can charge a customer for damaged equipment or for failure to return equipment.

I'd just like to make sure that I can do these things before I choose Squarespace, some pointers on the rough idea for how or links to specific articles about these topics would be greatly appreciated, I should be able to fill in the gaps if I can just get some good examples or reference material.



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Squarespace wasn't designed for this type of application. For example, you cannot recharge a payment method.

About me: I'm Paul, a SQSP user for over 18 yrs and a Circle Leader since 2017. I value honesty, transparency, diversity and good design ♥.
Work: Founder of SF.DIGITAL, providing high quality original extensions to supercharge your Squarespace website. 
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