If MacKay won the leadership, would a safe seat MP in the west or Ontario resign to allow him to take a seat in Parliament, or would he wait until the next election to contest a seat in Nova Scotia?
Someone will resign in a safe seat. The question is, who?
Off the top of my head (though not based on any information in particular), it's possible we could see Peter Kent step aside. He's been in parliament for a few terms now, and Thornhill is the safest non-rural CPC seat that close to Toronto, where the CPC wants to make inroads and where MacKay currently lives.
According to Wikipedia (so take that for what you will), MacKay's early endorsees from caucus are Ed Fast (Abbotsford), Blaine Calkins (Red Deer--Lacombe), and Dean Allison (Niagara West). All are MPs serving their 5th or 6th terms representing safe CPC seats, so they could all conceivably step aside. I'm not aware of any connections MacKay would have to any of their ridings, although that's not necessarily a deal breaker.