Updated September 28, 2026
An owner with four buildings called me convinced he had a pricing problem. He didn't. He had a sequencing problem. He'd already decided — correctly, for his situation — to sell piecemeal rather than as a package. What he hadn't decided was which building to list first, and that decision was costing him more than any pricing dispute would have. He'd been sitting on it for eight months.
Whether to sell a portfolio whole or piecemeal is a packaging question, decided by geography, asset coherence, and buyer-pool overlap across your buildings. Once you've landed on piecemeal — because your buildings are heterogeneous, because you want to keep some of them, or because your liquidity needs are staged — a second, separate question appears: order. Sequencing is not a smaller version of the packaging decision. It runs on its own logic.
If one building in your portfolio has a difficult tenant situation, visible deferred maintenance, or a compliance gap, it is worth strong consideration as your first sale rather than your last. The reasoning is about your own bandwidth, not the market: a problem building consumes a disproportionate share of an owner's attention and energy. Every month it sits unsold, it is pulling focus away from properly preparing and marketing the buildings that are actually ready to perform. Selling it first — even at a price that reflects its condition — frees the owner to give the stronger buildings the preparation they deserve instead of running all four processes at once, exhausted, with the hardest one eating the most time.
The opposite sequencing argument is just as real for a different kind of owner: sell your cleanest, most straightforward building first to generate a fast, confident close, proof to yourself that the process works, and cash in hand before tackling anything more complicated. This works best for an owner who is newer to selling, anxious about the process, or who wants the resulting sale experience — competent broker, clean escrow, no surprises — before taking on a building with more moving parts. Neither approach is universally correct. The problem-first sequence optimizes for total portfolio outcome. The easy-first sequence optimizes for the owner's confidence and cash-flow timing. Know which one you're solving for before you choose.
Buyer demand shifts by asset profile, not just by market cycle. If one building in your portfolio is post-1995, Costa-Hawkins exempt, and stabilized — the exact profile institutional and private equity buyers are competing for right now — that building should not be sitting fourth in line behind three pre-1978 properties simply because of the order you happen to have thought of them in. A building that fits current demand loses value the longer it waits behind buildings the market wants less urgently this quarter. Sequencing should follow demand, not habit.
Selling more than one building can push gains across tax years in ways that change your total liability, especially if some sales are straight and others are 1031 exchanges running on their own clocks. This is not a decision to make from a sequencing framework alone — run the specific combination of sales and timing past your CPA before you commit to an order, because the tax consequence of selling two buildings in the same calendar year versus two different years can be substantial and is entirely specific to your basis and income position.
Whichever building you list first, the preparation mistakes that cost LA sellers the most apply to each sale independently. A seller managing four sequential transactions is more likely to rush preparation on the later ones out of fatigue. Build the sequencing plan with that risk in mind — if you know your energy for careful preparation will decline by the third sale, put the building that most needs a careful process earlier in the order, not later.
It's worth saying plainly: sequencing decides the order, but it doesn't change what each individual sale requires. The complete process for selling a multifamily property in Los Angeles — pricing, preparation, marketing, escrow — applies in full to every building in your portfolio, regardless of where it falls in your sequence. Owners sometimes assume that because they're running multiple sales, later transactions can move faster or skip steps because "we've done this before." The market doesn't grade on a curve for experience. Each building gets its own diligence period, its own buyer pool, and its own preparation requirements, and treating a later sale in the sequence as a formality is exactly how a sequencing plan that looked smart on paper produces a disappointing result on the third or fourth closing.
One failure mode is worth naming directly: an owner who spends so long perfecting the sequencing decision that no building actually gets listed for months. The framework in this guide is meant to help you choose an order quickly, not to replace action with more analysis. If you've scored your buildings honestly and two of them come out close, it rarely matters which one goes first — what matters is that the process starts. The cost of a slightly suboptimal sequence is almost always smaller than the cost of a portfolio that sits unlisted for another two quarters while the owner keeps re-running the comparison.
Score each building on four dimensions, one to five: condition (how much prep work does it need), tenant complexity (any pending issues, difficult tenancies, compliance gaps), buyer-pool heat (how actively is this profile trading right now), and personal attachment (how emotionally difficult is this specific sale for you). There's no universal formula for combining the four — an owner solving for total portfolio value weighs buyer-pool heat and condition most heavily; an owner solving for their own bandwidth weighs tenant complexity and attachment most heavily. What matters is scoring all four deliberately instead of defaulting to whichever building happens to come up in conversation first, which is how most undecided sequencing actually gets decided.
The owner who called me convinced he had a pricing problem sold the difficult building first, at a fair price reflecting its condition, and had his best two years of net proceeds on the buildings that followed — not because the market improved, but because he could finally give them the attention a sale actually requires. Sequencing is not a delay tactic. It's the first real decision in a multi-building sale, and it's usually more consequential than the pricing conversation that follows it.
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Should I sell my worst building or my best building first?
Both are defensible, for different reasons. Selling the problem building first frees your attention for the rest of the portfolio. Selling the easiest building first builds confidence and generates fast proceeds. Choose based on what you're actually solving for.
Does selling multiple buildings in the same year cause tax problems?
It can, depending on your basis, income, and whether some sales are 1031 exchanges. Run the specific combination past your CPA before committing to a sequence — this is not a generic answer.
What if all my buildings are roughly the same condition?
Then buyer-pool demand should usually decide the order. Sell into active demand first; hold the buildings the market wants less this quarter for later in your sequence.
Michael Sterman is Senior Managing Director Investments at Marcus & Millichap.
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