2. Square - Get Organized

Items - this is what you're selling. You will be able assign taxes to Items. Examples of Items you can sell when all payments are due on a single invoice include "days", "peak season days", "weeks". You may want to create a "Security/Damage Deposit" item. Keep in mind that Square does not support Security Deposits per their documentation. Square allows you to issue refunds up to a year after invoicing. Keep this in mind if you're receiving full payment more than a year before your guest checks out. You will have to return the deposit using another method.
Locations - These cannot be deleted so be sure you create locations that you want and need. All invoices, taxes, items, bank accounts are associated with Locations. If you have more than one vacation rental property, you may want to create a Location for each. If the 2 properties are in the same area and use the same bank account and pricing, you may want just one Location. But even if they do share the same bank account and pricing, you can still create a Location for each. Shorter Location names are easier to read/recognize in the various drop-down menus where they are displayed.
Categories - Used for reporting. Assign each of our vacation rental properties to its own category.
What’s your billing schedule? 3 payments with deposit due now, rental payment 1 + tax due 60 days before arrival and rental payment 2 + tax due 30 days before arrival? Or maybe deposit due now and full payment and tax due 60 days before arrival? This information will help your build your invoicing schedule.
Are any of the “items” you're selling taxable? Know the various tax rates you’ll be charging. What are the names of these taxes?
Know the “Locations” you plan to use. Locations share the items and the tax rates with those items. Your bank accounts are assigned to “Locations”. Your invoice contents are assigned by “Location”. Once you create a “Location”, you CANNOT delete it! Think about this before you clutter your drop-down choices when building a “Location”.
Know the “Categories” you plan to use. Use this term to define the specific property you’ll be issuing invoices. Categories can be used for building reports through Square.
Do you want to have a message that shows up on every invoice? Perhaps encouraging payment be made by check instead? Remember these standard messages will be on each invoice associated with the Location that uses this invoice.
Do you have a logo image file to add to your invoice?
What name, address, phone, Web address do you want to show on your invoice/receipt for each “Location”?
Get your various Social addresses/user names together so that you can include them on your invoice.
Know your bank account information to receive Square payments and issue refunds per “Location”.