Prior research has documented the reemergence of predatory land contracts in majority-Black neighborhoods in the wake of the foreclosure crisis. Though land contracts facilitate property transfers involving lower-value properties and credit-constrained households, they are less regulated and often include risky terms. This paper investigates outcomes associated with properties sold using land contracts signed between 2008 and 2015 in Detroit, leveraging real estate transaction, tax foreclosure, and eviction and land contract forfeiture records. We also assess outcomes for the broader portfolio of properties purchased by large contract sellers. We find that sales by large contract sellers are generally associated with higher odds of near-term failure. We also find that investors using contract sales withheld property taxes on much of their inventory, consistent with a short-term triage-based business strategy. Conversely, the single large non-profit contract seller in our study had a far higher rate of success compared to all other contract sales. These results provide evidence of negative outcomes for sales initiated by problematic entities and supports arguments for stronger regulation of land contracts and upstream interventions to prevent predatory investors from acquiring discounted homes from public and institutional sources.