Documents

Receipts, invoices, signed agreements, permits and insurance policies live as ordinary files in a folder on your computer, by default Documents → Rentalist Documents. Rentalist files them and keeps track of what's attached to what. It doesn't lock them away: open, copy, or hand any of them to your accountant, without Rentalist even being open. The documents are stored as ordinary files, with no container, no encryption, and no proprietary format, so your paperwork stays readable whether or not you're still using Rentalist. If a document is sensitive, protect the folder the way you'd protect any other folder on your computer.

Each property gets its own folder. Inside it, documents tied to a year sit under that year (Receipts, Invoices, Contracts, Incidents), and documents that belong to the property itself, rather than to one year, sit in a Property File folder: permits and licenses, insurance policies, and anything filed as Other.

You pick the type when you add the file and, for anything that isn't a receipt or a contract, the year it belongs to. Getting it wrong isn't a problem: nothing about the filing changes your books. A receipt or a contract is filed with the record it belongs to, so it takes the year of the expense or the booking you attach it to. Attach one to a record from a different year and Rentalist moves the file into that year's folder, and says so.

There are three ways, all with the same result:

• From an expense. Drag a receipt onto the expense form, or choose a file. Files dropped on a new expense are attached when you save it.
• From a booking. Open a direct booking and use Add a contract. Files dropped on a booking you haven't saved yet are attached when you create it. Platform bookings don't have the section.
• From the Documents screen. Pick a type under "File what I add as." Everything except a receipt or a contract is then asked "What year is it for?" The box starts on this year, but it's yours to change, so a permit you found in a drawer doesn't have to land in the wrong folder. Then drop files in or use the picker. "Attach to…" links a document to a booking or an expense afterwards.

If you add the same file twice for the same property, Rentalist recognizes it and keeps one copy. If that copy has gone missing from the folder, re-supplying the file puts it back. One receipt can belong to more than one expense: a single slip covering, say, hardware and cleaning supplies is entered as two expenses, and you attach the same file to each of them.

A receipt or invoice you file against an expense is renamed to match that expense: the date, what it was for, and the amount, so 2026-04-12_Plumber-repair_385.00.pdf tells you what it is before you open it. A contract you attach to a booking is renamed from the stay instead: Sandy-Lane_Contract_Thompson_06-14-to-06-21_2026.pdf, which is the property, the guest's last name, the dates, and the year. Each file is named once, when you first file it against a record. Attaching it to something else later never renames it again.

This is on to start with. If you'd rather it didn't, turn off "Rename documents to match the expense or booking they belong to" under Naming your files on the Documents screen. New files then get Rentalist's standard name instead, made of the date the document is filed under, its label, and in brackets a short fingerprint of the file's own contents, which is how two files filed on the same day under the same label stay apart and how Rentalist recognizes a file you already have. It's one setting for the whole folder, and turning it off never renames anything already filed.

Rentalist never deletes anything from your documents folder on its own. Restoring a backup doesn't remove files. Deleting a booking or an expense doesn't remove files; it just drops the link, and the document stays on the shelf. The only way a file leaves the folder is Delete file…, which asks first.

Attaching a document to a past booking or expense works even when that year is locked, with no unlock prompt. Filing paperwork doesn't change a single number, which is what you want when an old year is being questioned and you need to put the agreement in front of someone.

• File not found: the file was moved, renamed or deleted outside Rentalist. The row tells you where it was last seen. Locate… points Rentalist at its new home.
• Temporarily unavailable: the file lives in a cloud folder (iCloud Drive, OneDrive) and isn't downloaded to this computer right now. Open the folder, let it download, and it comes back on its own.

"Re-check my documents folder" re-reads everything and clears up anything that's moved. If Rentalist can't find the folder at all (you moved it, renamed it, or the drive isn't connected), it stops filing new documents rather than making a second folder somewhere else, and asks you to point it at the right place. Nothing already captured is lost.

On the Documents screen, above your list of files, is Permits & renewals: a short list of the paperwork the rental carries, such as permits, licenses, insurance policies, property tax bills and inspections. It's a list of dates, not a filing cabinet. It doesn't hold the documents; it just remembers when each one runs out. Each item takes:

• What it is: your own words, for example "STR registration."
• Type: Permit, License, Insurance, Property tax, Inspection, or Other. For property tax and insurance, the date also tells your Cash Flow Forecast which month that bill is due in.
• Permit or license number (optional): the number on the permit itself. The row shows it with a Copy button, so it's at hand for listings, ads and correspondence. The number a tax office knows you by is a different one, and it goes in "Your number with them" on that payee in Settings → Fees & Taxes.
• Renewal or expiry date: the only field the reminder needs. Leave it blank and the item still sits in the list, but never reminds you.
• Estimated renewal cost (optional): what you expect it to cost. Leaving it blank means "I don't know," not "$0": an item with no estimate shows no figure and puts no line in the Cash Flow Forecast.
• Linked document (optional): points at a file already on the shelf. Nothing is copied or moved.
• Note (optional): the agent's name, the office you renew with, whatever you'll want.

What it does with the dates. Starting 30 days before a renewal date, the Dashboard says so. Snooze pushes it to the next check-in: 14 days out, then 7, then about once a week, right through a date that's already passed, until you move the date or delete the item. There's no way to turn it off for good, because an expired permit can take a listing down. Renewing something is your job to record: the app never rolls a date forward on its own.

Add as expense. Once you've paid for a renewal, this opens the ordinary expense form already filled in with the item's name, and your estimate if you recorded one. Nothing is saved until you press Add Expense, you pick the category yourself, and the renewal item is left exactly as it was. The expense and the reminder are two separate records.

The list belongs to the property you're on, and lives in your settings, so it travels in a Rentalist backup, unlike the documents themselves.

Your documents folder is not inside Rentalist's backup file. A Rentalist backup covers your bookings, expenses and settings; it does not carry your receipts and other documents. Keep the folder somewhere that's regularly backed up, such as Time Machine on a Mac, File History on Windows, or a synced folder like iCloud Drive, Dropbox or OneDrive. That is the protection that survives losing the computer.

When you move to a new computer, restoring a backup brings your bookings, expenses and settings across but not your documents. Copy your Rentalist Documents folder over to the new computer as well. Then open Documents and Rentalist will offer to re-attach the files it finds sitting in the folder. Nothing is attached without you saying so, and the offer doesn't expire.

If you've already connected your mailbox for inquiries (see Inquiries from Email), you can turn on "Look for receipts I email myself." Photograph a receipt, email it to yourself, and it appears in a review tray on the Documents screen with the attachment ready to file.

There's no code word to remember. Rentalist looks for messages sent from your own address, and addressed or copied to it, that carry a photo or a PDF, or that have no photo or PDF attached but read like a receipt or an invoice. The subject line isn't a trigger; it helps suggest a label for the document, which you can edit before you file it. An iPhone photo is converted so it opens anywhere.

Forwarding an order confirmation works too. When an email you send or forward to yourself has no photo or PDF attached and reads like a receipt or an invoice, the email appears in the tray, saved as a PDF you can open and file. Pictures in the email that are stored on the internet aren't downloaded, so they're missing from the PDF. Skipped: shipping and delivery notices, emails from a booking site such as an Airbnb confirmation, and any email that doesn't read like a receipt. Sending a guest a contract or another document you want kept? Attach it as a PDF or a photo and Cc yourself on that email, and it comes into the tray like a receipt. Using Bcc doesn't count; use Cc.

• Nothing is filed until you press File it, Attach to an expense… or Add as expense. Dismiss removes it from the tray and never touches your mailbox.
• It reuses the same read-only connection as inquiry email. Rentalist can't change, move, delete or send anything.
• Looking at messages from your own address is a filter to keep the tray tidy, not a security check. Anyone who can send mail that looks like it came from you could put an item in the tray, which is the reason nothing is filed until you press a button.
• Each item starts with a Type, such as Receipt, Invoice or bill, or Contract or rental agreement. Rentalist picks it from what the document says, its file name and the email's subject. When it can't tell, it picks Other. Change it with one click.
• Attach to an expense… files a receipt or an invoice from the tray onto an expense you already recorded. Expenses that match what was read, the same amount and payee, are listed first.
• Rentalist checks your mailbox when you open it and once an hour while it's open. Check now checks right away and tells you what it found, including why an email it checked wasn't picked up.

A receipt or an invoice sitting in the review tray, or one filed on the Documents screen with no expense on it yet, is read by Rentalist so it can suggest what to type. That includes a photo you drag onto the Documents screen yourself and file as a receipt. The reading happens on your own computer. Nothing is uploaded, nothing is sent anywhere, and no outside service is involved.

It looks for the vendor, the date and the total, and shows you what it found, for example "Read: $48.75 · Home Depot · Apr 12, 2026." Press Add as expense and Rentalist files the receipt and opens the ordinary expense form with those fields already filled in and the receipt attached. Every field is yours to change, and no expense exists until you save the form. Close it without saving and you're left with a filed receipt and nothing else. Read again reads a receipt one more time and shows what it found; it changes nothing else.

Check the amount. Compare what was read with the receipt in your hand. A smudged digit reads wrong more often than a missing one. A PDF with real text in it is read directly. A scanned PDF or a photo is read from the picture, and a dark, crooked or creased one can come back with nothing worth suggesting. Rentalist would rather leave a box blank than put a wrong number in it. Either way the receipt is filed, Add as expense works, and the form simply opens empty for you to fill in.