5 min read

Spend just minutes a week to earn thousands a month

You're about to connect and automate everything digitally. Hold tight.
Spend just minutes a week to earn thousands a month

Imagine you have a portfolio of seven properties. And imagine if everything you needed was on paper.

Every property tax bill. Every mortgage statement. Every financial forecast. Every lease.

Now take that and imagine every payment is made by check. Seriously imagine it. I get the shakes when I do.

We're going to build a digital ecosystem. It will your life easier when you have one property. It'll make your life much MUCH easier when you have seven.

Bonus: everything I'm going to show you is free. Or almost free. And I'll walk you through how to structure each piece of your digital ecosystem. By the end, here's what your digital ecosystem will look like:

You will need:

  1. A dedicated online bank account. One per property.
  2. An online file storage solution. Just one.
  3. An online accounting software program. Just one.
  4. A by-the-hour online bookkeeper. Just one.
  5. An online spreadsheet. Just one.
  6. A dedicated email account. One per property.
  7. A dedicated credit card. One per property.

Let's go through why for each of these and some recommendations.

A dedicated online bank account

Keep your personal and rental money separate. I can't stress this enough. Yes, you will have another bank account to manage. And that means you'll need a 'float' (money) in both. It's worth having one bank account per property.

Open a separate account before you put an offer in for a property. Every dollar, even your down payment, should come from this account. Everything is recorded and trackable.

Whichever bank you use for your personal account is a good option. It's easy to open. It's easy to transfer money between accounts. It means you only log in to one place for your personal and rental finances.

An online file storage solution

You must store every document, every bill, and every receipt here. You must structure your folder system and stick with it. You must use the app version of the storage program to capture scans and images.

I'm using the word 'must' intentionally. It's better if you're all-in. If you're half online and half paper, you'll get confused and frustrated.

I recommend Box or Dropbox. Both have good desktop and mobile app versions.

Secure File Sharing, Storage, and Collaboration | Box


I'm less militant about the folder structure. Here's what I use:

Property address

One-off documents [includes things like purchase & sale, deed, plot plan, appraisal...]

Regular documents


Rental agreement

Bank statements

Credit card statements

Property tax

Water & sewer


Other receipts

LLC filing

Financials [bookkeeper statements etc.]

Date every file in the same format. Most property documents are monthly or annual. Label them so you can find them easily.

Share specific folders with specific people. Your spouse. Your bookkeeper. Your lawyer. You don't need to send files around by email. Give 'read' (vs edit) access as needed.

An online accounting software program

You're going to have lots of items going into and out of your rental property's bank account. This software connects to your rental property bank account (not your personal). Your bookkeeper will use this software to classify every item for an accurate end-of-year statement.

Each property should have one bank account associated to it. You can change settings to allow your bookkeeper account-by-account access.

Three alternatives for you: Freshbooks, Wave Apps, Zoho Books. But there are plenty out there. Prices range from free to $10 per month. I personally use Wave Apps. It's good enough. And it's free (for my set up).

Invoice and Accounting Software for Small Businesses | FreshBooks

Online Accounting Software - USA | Zoho Books

Wave Financial: Financial Software for Small Businesses

A by-the-hour online bookkeeper

Find an online bookkeeper who knows the accounting software you plan on using and the basics of real estate. Upwork is a solid resource to find the right person. You can look at test scores, reviews, rates, and more. I pay $15 per hour and my bookkeeper gets paid automatically. It's great value-for-money.

Upwork | Hire Freelancers. Make things happen.

An online spreadsheet

Use google sheets - a basic version of Excel. You will need a Google (Gmail) account.

Create a monthly calendar of regular bills or financial tasks you'll need to complete. You can put a link and what needs to be done.

Here's my example (column C has descriptions of the tasks and links):

Tasks I have listed include uploading property tax statement; uploading bank statements; scanning, paying by check, and uploading landscaper invoices (he's old school), filing annual reports for our LLCs and so on.

This task list looks a lot. Each task takes me 30 seconds. Being organized - links, passwords - is why I'm fast. There's task automation software that you can use to make it even faster. Keep pushing the automation boundaries.

Pay all your bills online with automatic payment. You'll never get late fees. You'll save yourself another task.

On a separate google sheets tab track your credit card spending line by line and any unusual bank charges for each property and bank account.

Share your google sheet with your bookkeeper so they can reconcile what they're seeing in the accounting software.

Your bookkeeper - particularly if they're international on Upwork - simply won't be able to categorize some items for your year end statement. You need to manually step in to help them. If your credit card says "Home Depot $78.94" your bookkeeper won't know what it is. If you write a check for a new washing machine, your bookkeeper won't know what "A&D services $463.02" is.

Aim for less than ten unusual bank charges and un-itemized credit card amounts per year, per property. If your property manager is doing their job, 95% of all expenses will be approved and managed by them.

A dedicated email account

Your going to get a lot of emails. Bill reminders. Bill payment confirmations. Property tax notifications. Questions from your bookkeeper.

If you've set everything up on automatic payment most of these emails will be uninteresting.

Set up an email account for Property.ABC@gmail.com. It's good practice, especially if you have lots of properties.

If you try and use gmail filters (as an example) instead of separate email addresses, it may not work. If you have many properties in the same area, gmail won't necessarily be able to filter by property.

If you want to go 'beast mode', use Asana automate tasks from your inbox. I'll leave it at that for the curious among you.

A dedicated credit card

This is an optional item.

There's usually a 2-3% surcharge to pay regular bills with a credit card. That's to cover credit card fees. If your town or city doesn't, it absolutely makes sense to use a dedicated credit card.

Otherwise you should have so few expenses not covered by bills or your property manager that it's barely worth it.