I began doing professional web design in 1993 (when I was in high school and the web was 2-years-old). I worked as a professional web designer for about 10 years before getting my PhD in computer science. I have written books on web design and taught it since 1999. My research is all web-based and my most recent book is focused on essentially doing forensic analysis of social media accounts. It includes a section on the internet archive, and I have done expert work for a SEC case using the internet archive and searching for material online as is described in this case. Depending on how large the site is, I think it is worth identifying the relevant sections at different time points (usually around the points of a redesign) and doing an exhaustive page-by-page search for relevant content. This is usually a relatively quick process once you know what the pages look like and where the content might be. The internet archive also has an advanced search that can be used to look for specific phrases within archived pages. If the website owner has produced their own archived versions of their site, these can easily be searched with simple code for any mentions of the phrases of interest.