Does splitting a deal into asset and share components make closing more complicated?

Generally, yes, and it's worth going in with that expectation rather than being surprised by it. A split deal usually means two sets of purchase documents instead of one, potentially different consents — landlord or contract counterparty consent for the asset piece, and possibly the selling corporation's own shareholder approval for the asset piece if it represents substantially all of that corporation's property — plus separate tax filings, since the asset portion may involve a GST/HST election while the share portion is reported as a capital transaction.

The added complexity isn't just paperwork volume. Cross-conditioning both pieces so that neither closes without the other, coordinating financing that may need to fund both transactions simultaneously, and making sure due diligence has actually covered each piece separately rather than treating the whole thing as one undifferentiated deal, all take more coordination than a single, straightforward purchase.

None of this means a split structure isn't worth doing — often it's exactly the right way to achieve what buyer and seller each actually want. It just means building in a proper closing checklist and enough lead time for two coordinated transactions rather than one. A business lawyer managing both pieces together, rather than treating them as separate files, is what keeps the added complexity from turning into delay or error at closing.