Canadian snow birds have a long history on Maui, particularly in South Maui. In the 1960's, many condominiums throughout Kihei were developed by Canadians, and they were largely purchased by Canadian nationals who became part-time Maui residents. Some of those units are still owned by the same families today.

Another major wave of investment by Canadians happened when the Canadian dollar surpassed the US dollar in value. With lower price points on real estate all over the world, buyers with cash scored on prime Maui real estate, which has multiplied in value since then.

Many Maui condominums that were built prior to 1989 were granted an exception which allows them to be rented out to non-residents on a short term basis, which are known as "short term vacation rentals." This allows owners who are on Maui only part of the year to earn cash flow by renting out their condominium to vacationers when they are at home. The existence of these rentals has further increased the values of the condominium beyond typical market forces.

Since the fires, housing has become a high priority for State and County lawmakers, and the exception could be threatened.

Canadians collectively own more than 70% of Maui's central valley. In late 2018, "Mahi Pono", a partnership between a California-based agricultural company and the Public Sector Pension Investment Board (PSP Investments) purchased 41,000 acres of former sugar cane lands from plantation owner Alexander & Baldwin.

Mahi Pono, which loosely translates as "to cultivate the land responsibly," produces citrus fruits, coffee, avocado, and farms cattle. 

PSP Investments invests on behalf of employees in Canada’s federal public service, the Royal Canadian Mounted Police, the Canadian Forces, and the Reserve Force,