Better information design
In addition to being unsearchable, the PDF applications were hard to scan. Each had a its own design, the information was in different places, etc...
Our first concern in building the apartment page was clarity and consistency: we pulled out the most salient info - nearby transport, amenities, the often-arcane eligibility requirements the lottery, and offered clear calls-to-action: "apply" or "more info". The application process still had to go through Housing Connect, but we built a robust FAQ for each lottery that made it easier to get questions answered.
We also supported favoriting, so the already-difficult process of sorting and applying would be made a little easier.