The City of Oskaloosa set up the Oskaloosa Housing Trust Fund to create a continuing program to increase reinvestment in its housing stock . Although the trust fund was established by City ordinance, a committee consisting of significant donors and five members from the community at-large governs the trust fund. During its first year the trust fund received grants from the Iowa Department of Economic Development and the Federal Home Loan Bank. A local fund-raising effort, transfer of the City's revolving loan funds for first-time home buyers and the demolition program enabled the City to capitalize the trust fund.

Before the start of the trust fund, the City had primary housing programs (first-time home buyer assistance and a demolition program). However, with the start of the trust fund, the number of programs has expanded and continues to grow. Programs now include a minor home repair help for lower-income homeowners and a rental rehabilitation loan fund. They have also added a speculative housing construction loan program and a program to buy and redevelop property . From these core programs, the Oskaloosa Housing Trust Fund diversified by partnering with the Oskaloosa Community School District. Through this partnership they developed a construction trades program for the high school. In partnership with the Oskaloosa Municipal Housing Agency, the trust fund provides added rental help in the community. And, they now have an incentive program to help lower income buy new homes.

The partnership with the school district expanded in January of 2005 when the trust fund agreed to take two decommissioned elementary schools from the district for redevelopment. They divided the first school lots and sold them to area contractors to build single family homes. The trust fund used a competitive process to select contractors to build the homes, and provided incentives to keep the price of the homes affordable. The second school building is being converted into fourteen senior housing units. The gym is being converted into a community center, and the playground area will be developed as a park.

The OHTF continues to grow and become a major force in the Oskaloosa housing market. In its first four years, the trust fund has leveraged its investment of about $2 million into a total investment in the community's housing stock exceeding $21 million.