Couch hopping is a significant feature of youth homelessness in the United States. Every year, half of youth ages 18 to 25 who experience housing instability report couch hopping--also known as couch surfing or doubling up. Emerging work suggests that in some intergenerational informal hosting arrangements, youth and their adult hosts can form meaningful and supportive relationships. However, hosts also navigate material challenges that could threaten the stability of these arrangements. Based on in-depth interviews with nine youth ages 17 to 23 in informal hosting arrangements and 10 informal hosts, we describe how increased household costs and lease and benefits restrictions can impact stability, and the strategies hosts and youth mobilized to address them. We place hosts' instability in the context of intergenerational poverty and structural racism, reframing material challenges as opportunities to strengthen the village of support youth need to make sustained exits from homelessness.