In theory you could automate generating the tiles, but you can't really automate downloading the dataset; it's enormous (hundreds of Go IIRC) and most of the time has to be checked by hand.
Depends on the coverage. If you wish to serve the entire world, it is indeed massive (~100 GB indeed); but from my experience, the updates are 1.automated and, more importantly, 2.incremental. Perhaps the technology has advanced since you tried it... (How do you even check 100 GB of data by hand? That seems impossible.)
That said, I am using the dataset for generating a map, but I'm only using a country extract - which only goes up to some hundreds of MB, and updates on the order of tens of kilobytes. Far more manageable.
