Summary: At our May WIN event, Uptown Properties' own Chris Shepard delivered a candid market update on where Portland's rental market stands heading into mid-2026. From softening rents and rising inventory to where the opportunities still exist for strategic investors — Chris broke it all down with real RMLS data and cycle analysis. Watch the full recording and see what it means for your portfolio.

If you own rentals in Portland right now, you've probably felt it, the market has shifted. Rents are softer, inventory is up, and the headlines aren't exactly inspiring confidence. But as Chris Shepard made clear at our May Westside Investors Network event, the data tells a more nuanced story and for the strategic investor, there's still plenty of opportunity.

Chris has been managing investments in the Portland metro since 2009 and has seen more than one market cycle. That experience showed in how he broke down what's happening right now and, more importantly, what to do about it.

Watch the Full Update

Watch Chris Shepard's May market update here

What Chris Covered

• Where Portland sits in the current market cycle and what history tells us about what comes next
• The latest RMLS data: what's moving, what's sitting, and what it means for owners
• How softening rents and rising inventory are affecting Portland landlords right now
• The sectors and submarkets that are still performing
• What strategic investors should be doing in this environment to position themselves for the next upswing

About Chris Shepard

Chris Shepard is a licensed broker in Oregon, co-founder of the Westside Investors Network, and owner of Uptown Properties, a Portland-based property management and brokerage firm. He has managed investments across the Portland metro since 2009 and owns property in multiple states including multiple 1031 exchanges and cost segregations. He brings an owner's eye to every market updat, because he's playing the same game you are.

Don't Miss Our Next Event

Our next WIN event is June 18th, Portland ADUs: From Permitting to Profit. Jordan Tietz, a local developer who has permitted 120+ units in Portland, is breaking down everything from zoning to cash flow.

Reserve your seat: PortlandADUs.eventbrite.com