I've seen that Destin video, but I don't get the feeling that he's thinking bigger than Apollo, which got defunded and halted. A continually occupied lunar surface base won't work if it has to get crewed and stocked by a Saturn V or SLS.
SLS and Orion exist because of Congress maintaining STS jobs. Starship HLS exists because of tight purse strings. Blue Moon exists because of lobbying.
When was the last time you watched or thought about a Starlink launch on Falcon 9? They happen multiple times a week without any fanfare. Starship depot refueling flights are meant to be even more boring than that. The bigger hindrance is the requirement to dwell in NRHO and wait for Orion to show up.