Does my landlord's attitude toward assignment affect what buyers think my business is worth?

Yes, often significantly, because if the business operates from a leased location, a buyer needs confidence that the lease can actually transfer to them, and a landlord known to be difficult, slow, or unpredictable about consenting to assignments introduces real uncertainty into a deal that has nothing to do with how well the business itself performs.

The nuance is that under Ontario's Commercial Tenancies Act, where a lease restricts assignment without the landlord's consent, that consent is generally deemed not to be unreasonably withheld, unless the lease itself says otherwise, but the lease's own specific wording controls first, and "not unreasonably withheld" still leaves room for delay, added conditions, or genuine disagreement about what's reasonable in a particular case. A landlord's track record and relationship with you personally can matter as much as the strict legal position.

If you know your landlord tends to be difficult, it's worth having a candid conversation, or at least understanding their likely position, before you're relying on a fast assignment to close a sale on schedule. A business lawyer can review your specific lease's assignment clause and help you gauge, and manage, this risk before it becomes a live issue in a deal.