Let me preface this by mentioning we were referred to the developer forum by the Square Support forum. We have little knowledge of creating Square APIs.
We are a nonprofit art gallery that primarily sells artwork. As such, we need to notate specific information regarding each painting that sells. The Artist’s name, the Buyer’s name, Painting title, etc. Currently, we enter all of this information into the “Notes” text box when making a sale through our POS System. This method gets messy fast, as different paintings and buyers might require different information to be put in, different employees might type that information in a different order, and it is difficult to organize on both receipts and our spreadsheets.
We have been looking through the various customizations Square allows for in their item menu, specifically Options and Modifiers. These allowed us to make options with preset values, like “Small and Medium” for a category called “Shirt Sizes”, etc. But that isn’t what we are looking for.
We are looking for a way to have Options pop up for making a sale, but instead of toggling or choosing from a list, We need an Option with an empty text box. An option for each of our requirements, one for Artist Name, one for Buyer Name, etc. So that our employees can just enter that information into each of the appropriate options when making a sale, rather than cramming it all into the “Notes” section. Something they can click on and type into, that will appear on the receipt and spreadsheets, just like how options currently function in Square.
After some searching, and calling Square Support, we realized there is currently no way to do this. It seems like such a simple thing; to have an option you can enter a custom value into at checkout.
We are inquiring to the Developer community wondering if software that has already been created is capable of this? And if not, where to start in regards to creating this software for ourselves?
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Based on the information you’ve provided, the following documentation will help answer your question:
Additional Documentation
Payment API: Process Online and In-Person Payments
Square Developer Documentation
Customer API: Securely Manage Customer Data
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Based on the information provided in the Square Developer Documentation, it seems that the functionality you’re looking for isn’t directly available through the Square APIs or SDKs. However, you might be able to achieve something similar by using the Catalog API and the Orders API.
The Catalog API allows you to create and manage a catalog of products and services, including items, variations, categories, discounts, taxes, modifiers, and more. You could potentially use this API to create custom attributes for your items, such as “Artist Name” or “Buyer Name”. However, these would be static and not editable at the point of sale.
The Orders API allows you to add functionality to payments, such as itemizing payments using custom line items or catalog objects. You could potentially use this API to add custom line items to an order at the point of sale, which could include the specific information you need to capture (like the artist’s name, buyer’s name, etc.). However, this would require some custom development work to integrate this functionality into your point of sale system.
It’s important to note that any custom development work would need to be done in accordance with Square’s API usage guidelines and best practices for collecting and handling personal information.
If you’re not comfortable with doing this development work yourself, you might want to consider hiring a developer or a development agency with experience in Square’s APIs and SDKs.
This answer was reviewed by @Bryan-Square.
If you are looking to hire a developer you can browse Square Specialist to find the right Specialist for your need. 
Bryan,
Thank you for reaching out. Looking into it further, because we use the Square Register, I don’t think our proposed query is possible at all. Even If we did go through a specialist to create a custom application that suited our needs, we would need to use third-party hardware to run the software, making our register obsolete. We’ve submitted an engineering request over the phone in hopes that this feature might be added in the future.
NSAA
Okay, yeah at this time running custom software on the Square Register isn’t currently possible. You could do this with other hardware but not the Register at this time.