By Ronnie Cook, Senior Vice President of Product Design and Strategy.
In college, I started playing Fantasy Football. For the uninitiated, it’s a simple game of analyzing past performance to anticipate future outcomes, played for bragging rights – or the fear of losing an embarrassing bet.
Playing in the early 90’s, however, was a nightmare. It started with buying a four-month-old magazine – information so stale we ran a constant risk of drafting an injured or retired player. Instant ridicule was guaranteed. Weekly updates weren’t much better. The day after a game, we’d hunt down a newspaper (remember those?) only to find stats like: WR – A. Harper 3 rec, 89 yds. Zero context. Zero insight.
Today, fantasy sports is a $27.8B industry expected to nearly double by 2030. This rise is entirely thanks to the Internet, which turned guesswork into a science. Now, anything you want to know about a player is live-streamed 24/7 with endless data, context, and expert analysis.
It’s about to be 2026. We have robot dogs, self-driving cars, and drones that can deliver pistachios to your backyard. And yet, in commercial real estate, we are still emailing property reporting packages each month.
We’re trying to anticipate future outcomes based on business plans that are six months old or more. Our financial and operational reports offer limited and stale data: zero context, zero insight. But unlike a Fantasy Football league, with millions – if not billions – invested, we have a lot more on the line than just bragging rights.
If your current data strategy is stuck in the 90s, here are 3 options I have seen companies use to beat the competition:
In this scenario property managers log in to your instance of accounting software to make operational and financial updates. You receive the benefit of robust real-time data and standardizations on things like chart of accounts, charge codes, tenant industries, and statuses. This greatly simplifies aggregating the data into a warehouse and expands your reporting options. However, the biggest con, beyond licensing and migration, is that you will need an administrator to maintain permissions and security as various accountants come and go.
All the major accounting systems provide ways to connect and get data out. Contact your property managers and request direct data access – whether via APIs, database copies, or scheduled report extracts. Like option 1, you gain robust real-time data however you lose the benefit of standardizations as each property manager can and will have different ways of cataloguing information. Depending on the number of outsourced managers or different flavors of accounting systems, aggregating the data into a centralized warehouse might be a large project.
If connecting to the source systems directly is not an option, then look to extract the data out of reports via a tool such as a submission portal designed for real estate. These tools allow for the intelligent data extraction from various reports such as rent rolls, trial balances, offering memorandums, lease abstracts, etc. While the amount of information is significantly less robust and frequent as options 1 and 2, getting the data abstracted and into a warehouse is a significant upgrade from the information being trapped on a file share or inbox somewhere. Look for a product that enables several data submission types, standardization of chart of accounts, and custom validations rules. Cherre’s Data Submission Portal (DSP) is doing just that.
Fantasy football players traded grainy newspaper clippings for live, 24/7 data streams because they knew guesswork was a losing strategy. In commercial real estate, relying on six-month-old business plans and static, once-a-month reports is the professional equivalent of drafting an injured player – and the stakes are infinitely higher than an embarrassing bet. It’s time to stop letting critical data languish in inboxes and on file shares. Whether through direct integration, managed software instances, or intelligent extraction tools, adopting a modern data strategy is the only way to move from managing by hindsight to leading by foresight. Don’t let your competition use 2026 technology to win a game you’re still playing in the 90s.
Ronnie Cook is the Senior Vice President of Product Design and Strategy at Cherre, where he leads the company’s product vision and roadmap. As a former executive in Real Estate Engineering at Goldman Sachs and former Head of Product and Services at Pereview, Ronnie brings a proven track record of delivering purpose-built solutions that solve real client challenges and turn complex data into intelligent, actionable insight.
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Multifamily has entered a defining moment. AI is no longer an experiment – it is becoming operational. During NMHC’s OPTECH 2025, leaders didn’t discuss hypothetical use cases; they showcased live deployments, automation wins, and the next wave of agentic innovation taking shape across leasing, operations, compliance, and portfolio performance.
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Whether through direct integration, managed software instances, or intelligent extraction tools, adopting a modern data strategy is the only way to move from managing by hindsight to leading by foresight.
