He Was Right in 2000, 2008, and 2020: Now He’s Saying to Buy

What if flat markets are actually the best time to build real wealth?

I left this conversation feeling oddly optimistic. The housing market feels stuck — prices and mortgage rates hovering with little drama — yet that stillness is fertile ground if you change how you look at opportunity. Think less about timing a big pop and more about quietly assembling a base of cash-flowing assets that will amplify future gains.

Why the stalemate matters

Picture a glassy lake. That’s the current market: sellers clinging to ultra-low mortgages, buyers waiting on rates to fall, and both sides paralyzed. It creates an equilibrium where competition thins. I was surprised to hear how similar today feels to the mid-1990s, when prices barely moved for years before a multi-year upswing. That kind of plateau is frustrating, but it’s exactly the environment where disciplined buyers can accumulate without getting into bidding wars.

Honestly, I hadn’t considered how psychological the whole thing is — sellers and buyers are both waiting for a nudge. Until that nudge arrives, patient investors have a choice: either sit out or quietly collect assets with an eye on decades, not quarters.

Two different plays for two different goals

One clear takeaway: your plan should match your objective. For someone building retirement wealth slowly, small multifamily and single-family buy-and-hold strategies look attractive right now. For operators trying to deliver quick returns to investors — the syndicators and institutions — the risks are higher because their timelines are shorter and debt structures tend to be tuned to market cycles.

The difference matters. Small multifamily (think 4–40 units) often sits with tired mom-and-pop owners who want out. Those sellers can create windows for creative financing, lower acquisition prices, and hands-on value-add work. It’s dirtier, yes, but that’s the point: someone has to do the work a lot of investors are unwilling to do.

Where the real deals are hiding

• Class C, workforce housing: Older buildings built in the 1960s–1990s with deferred maintenance often trade at steep discounts.
• Small multifamily units: Five- to thirty-unit properties with motivated sellers show the most distress pricing.
• Sleepy markets: Secondary cities that aren’t hot on every investor’s list can yield surprising cash-flow and long-term appreciation.

I found the stories about Buffalo and a 16-unit building particularly compelling. Low basis purchases later transformed into mortgage-free income and a Maui condo via a 1031 exchange. That arc — from modest, gritty purchases to life-changing outcomes — is the kind of narrative that stuck with me.

Financing is the differentiator

One practical surprise: fixed-rate, fully amortizing loans still exist for smaller multifamily if you look beyond the big debt funds. Local community banks and seller financing can be the bridge into long-term, conservative debt. That means you can buy now, lock in predictable payments, and sleep at night even if variable-rate markets become turbulent.

Creative sequencing matters. Buy with seller financing or a bridge line, renovate to increase rents, then refinance into a long-term fixed loan. That path requires effort and patience, but it transforms opportunistic buys into stable retirement engines.

The work that pays off

There’s an important mindset pivot here: returns won’t be handed to you by market tailwinds as they were in the last decade. Instead, returns arrive because you renovated, parceled out units, added secondary suites, optimized operations, or found an overlooked neighborhood. It’s the old-fashioned, hands-on approach — but with modern underwriting and patience.

Also, a simpler emotional lesson: grind now, relax later. If you can tolerate lower short-term cash flow in exchange for fixed-rate debt and stable principal reduction, you’ll own reliable income that compounds into retirement security.

Three practical moves I’d make after listening

• Build a buy box focused on smaller multifamily and workforce housing in second-tier markets.
• Talk to community banks and local sellers about creative financing before chasing bridge lenders.
• Be patient: wait for the right property, then do the renovation and refinancing dance that converts temporary risk into long-term stability.

What really caught my attention was the humility baked into the strategy. This isn’t get-rich-quick thinking; it’s get-rich-slow, deliberate accumulation. There’s a quiet joy in that. You don’t have to time the perfect pop to win. You just have to collect good assets, do the work, and give time a chance to do its thing.

When the lake eventually gets choppy — and it will — the assets you assembled while things were calm will feel like a secret advantage. That thought stuck with me long after the conversation ended.