Updating a resume is hard if you don't have everything already stored in a sqlite database.
The resume that you see in the resume page and in the pdf were both generated from a few scripts that makes queries on a sqlite database. All of the data related to my work history, skills, and education are stored in a local database on my machine.
Furthermore the repository has some scripts that move the generated pdf and markdown files into the repository for this site and then pushes it to github. Easy!