We are a small team planning a website rebuild plus SEO, and possibly some custom software later on. I keep going back and forth between hiring separate freelancers and working with one agency that covers everything. How do you usually decide which way makes more sense?

I went through the same thing last year. What helped me most was comparing how each agency described its process instead of its results. I checked whether website development, SEO and custom software were explained as separate services with clear deliverables or just listed as generic capabilities. One page I kept as a reference point was Enginuity, you can view how the services are split there, and I used that structure to ask other studios the same set of questions. The differences showed up quickly. Some could name timelines, reporting format and who exactly would be on the project, others stayed vague. I would also ask what happens after launch, because ongoing support usually matters more than the initial build.