Just for fun, a short blog post on this:
@djnavarro There, I solved it. I have two small small bash scripts that change all my rstudio settings to daily or teaching mode, so modified them to either create or remove a ~/.config/taeching file and then have my .Rprofile modify the startup message only if the file doesn't exist.
I also added a few different flags and it prints a random one. Yey!

@Drmowinckels Oh yeah that's a bit of a hack. My .Rprofile has a line in it that clears the screen (and with it the default startup message):
cat("\014")
After that, I write my own startup message like this:
cli::cli_alert(R.version.string)
cli::cli_alert(paste("Running under", utils::osVersion))
cli::cli_alert(paste("System time is", as.character(lubridate::now())))
@Drmowinckels That works fine in RStudio, but if you want it to work for R at the terminal you have to do a bit more work, so the actual "clear screen" code I use is
system2("clear")
cat("\014")