Optimizing time spent with bills, statements, receipts; paper vs electronic

[Paul Balyoz]

As an owner-landlord of 20+ single family homes across 3 states now, I am spending an inordinate amount of time handling bills, statements, receipts and other paperwork, both in physical-paper form and electronic. I probably spend 20 hours per month on this stuff. I want to optimize my time, find ways to automate, but I haven't found many good options.

If you receive bills & receipts & statements by physical-mail (USPS), or in person:

* must scan them into a PDF to file them digitally; then file-away the paper, or shred it.

* not everything arrives as paper, so if you file the paper away, you can't search your paper-files to find everything later - files are incomplete - unless you print every digital file you get, and keep TWO sets of files (physical + digital)! That's a lot of extra work, and wasteful, so much bulk paper - stored in many file cabinets, file folders, banker's boxes to rotate your files every year, paper-cuts, etc.

* while looking at any page of paper, it takes work to figure out what property-address or LLC is that it goes with! Many companies don't print the service-address on the bill/statement, they think you're a homeowner with 1 property. I had to make a lookup-table file on my desktop, so I can map "account ending in 1234" to "500 S Property Avenue, inside your XYZ LLC". It's a lot of extra work for half the paper items I receive. Same thing for insurance, bank & credit-card & lines-of-credit statements - a lookup table is the way to go, just slow & annoying.

OK, so let's go all digital! That's the modern way, right? Check the "bill me digitally" option, or "paper statements," or whatever each company calls it. This can even save a few dollars each month (some banks charge a fee to mail you paper-statements). But this causes other problems:

* half the companies send no notification when each bill or statement is ready on their website.

* the ones that do notify you, it goes to email - how often do you keep up with your email? (I have trouble with this personally).

* the notifications are often cryptic about what it is - "a new document is available in your portal," with no info about whether you care about this document. Is it a statement? a bill? random FYI? do I need to take action or not? HOA's do this all the time. I care about the bills, and about changes in HOA fees, but I don't care about voting, or many other communications from the HOA.

* fetchiing the document is non-standard and confusing: find the right URL & login & password for them, navigate the completely-inconsistent (and often confusing) web site -- every company is different from every other -- to find where the documents are; find the newest document; try to figure out if there's more than one that arrived, how many should I download? which ones do I already have?  Download the document; open the document; read the document; decide what to do about it.

* now that you downloaded the document, where do you file it away in your system? You have a hierarchical standardized storage system for all your digital files, right? Is it in Dropbox, OneDrive, or another cloud system? Where do you file this thing away, in its proper place, so you can easily find it later? Does a receipt go into the property-specific LLC's area, or the outermost-holding-company-LLC that pays all the bills? Or is it related to a specific property manager company? ...who manages many properties, so where does their folder live? If a utility company sends you a shut-off notice, does that go into the property folder, or the property-manager folder, after you handle it? Or both?

* HOA web sites are the worst - for properties you have that are in HOA areas. I don't recommend buying properties in HOA's, but I have 5 of them myself. Two of the properties have TWO HOAs each. HOA web sites are the most convoluted and confusing outdated-looking crappily-designed and organized data-management-systems out there. And every one is completely different from every other one. With one site, I could not figure out how to change my password for weeks - I probably spent more than an hour looking for how to do that. I finally had to call the HOA management company for help, and they walked me thru the 10-step process for finding the spot where you can change your password! Please note that I was a full-time software engineer with a 39-year career before I retired a year ago; my last 3 jobs were building and maintaining huge custom web sites for large companies. If I can't figure out site navigation, something is terribly wrong.

I finally realized something:

The postal-mail-system uses a common user-interface! No matter who sends you documents via postal-mail, the way you process them is always the same:

1. if it arrived in your mailbox, then it's queued for you to process it - you won't miss it. (It sits on your desk until you address it). Unlike email, text messages, and calendar appointments, if you don't react to it immediately when you're not ready to address it, then you can easily miss it and forget about it. Paper is in-your-face until you deal with it.

2. it comes in an envelope. You open the envelope and pull out its contents.

3. the contents are folded pages of standard-sized paper. Unfold them, and staple them together.

4. read the paper to understand what it's about.

5. Decide what to do with it:  scan and file it digitally? toss/shred it? or file it in your "reference" drawer for later use?

This is not true for digital documents / web sites. There's no consistency, no standards, no queuing system to make sure I miss nothing.

I just wish the processing steps were easier for digital files. I want an application that can log in to any web site, and navigate any crazy arrangement of pages & links, download any file, understand what that file is about, and file it away automatically in the right place in the cloud.

I actually wrote a Perl script that does the "file it away in the cloud" part properly, for about a hundred different documents. It takes work to maintain that script, though, it's not something a non-programmer could maintain; plus, I have to already have interpreted the meaning of each document, and named the files in a unique way that includes the date, so that the Perl script files it away in the right place.

If I could automate the web-site interactivity part, and connect that to a calendar-based trigger of some sort (on the last day of the month, login to THESE sites and download all the files), that would go a long way to freeing up my time.

As a real estate investor, I want the freedom to have 10X the properties I have today. I don't think I could handle 10X of all the paperwork I have to deal with today! It would be more than a full-time job at that point. If I could automate it better, so it took only (let's say) 2 hours of my time per month, then I could handle 10X of that amount of work.

How do you handle all the paperwork of your life? Digital, and physical?

Have you found any great automations that help you with this?

What can we do to figure out a better system, to handle all this?

What can we do to make all HOAs use the SAME WEB SITE PLATFORM, so that at least we could memorize how to download documents quickly every time? Or optionally set a "just email me the PDFs, I waive my right to privacy," because email is generally more secure now than it used to be, and/or I don't care about privacy for my HOA statements.

I'd love to hear what you think.