Ideally with a closing structured so that funds are committed through an escrow that releases on visa issuance, timed before the winter booking calendar opens. Closing outright before the application is possible but leaves the couple owning a business they may not be able to run.
Let the booking calendar and the escrow terms set the date
The management company's revenue concentrates in the ski season, and owners open their booking calendars months ahead. A change of hands in the middle of that cycle is risky for retention, so the natural target is a closing in late spring or summer, with the couple on site before bookings peak. The immigration side needs the investment committed before the interview, which the FAM allows through an escrow that releases only on issuance of the visa, provided the terms are written so that the couple cannot simply walk away.
Negotiate that escrow with the seller early, since sellers often prefer certainty and may want a larger deposit in exchange. Sequence: sign the purchase agreement with the escrow terms, sell the chalets, fund the escrow, assemble the source-of-funds file, apply for the visa, close on issuance. If the seller insists on an unconditional closing, the couple should understand that a refusal would leave them owning a Vermont business they cannot manage in person.