Identify the business and negotiate terms first, then structure the agreement with escrow conditioned on visa issuance, then complete the source-of-funds documentation, then apply. Do not close the purchase before applying, and do not apply before the funds are actually committed.
The sequence protects the money and satisfies the rule at the same time
The tension is real: the officer needs to see money irrevocably committed, and the buyer does not want to have spent it on a business he may not be permitted to run. The escrow structure resolves it, which is why the sequence matters more than the calendar. Work in this order: letter of intent and due diligence; purchase agreement drafted with the visa condition; funds gathered and traced into escrow; application prepared and filed; visa issued; escrow released and closing completed. Interleaving these steps is what creates problems, particularly paying a large non-refundable deposit early to secure a deal. Note also that a Canadian citizen needs an E-2 visa issued by a consular post; the border-crossing convenience that applies to TN and L does not extend to E.
Hypothetical example: a fire-suppression inspection business has a contract contingent on its owner’s authorization. The review should decide which commercial contingencies should be set before consular processing, using licence requirements, escrow conditions, fund trail, contract terms, and sequence. Work backward from the controlling evidence, then allow time for correction, adjudication, and any admission or consular step. Keep a written chronology of commitments and permissions. The planning failure is that treating a deal as fully reversible can undermine proof of investment risk. Do not let a commercial schedule outrun the immigration record.