Re-assurance for number of launches
On average, Falcon 9's launch about three times per week. SpaceX are applying their experience with Falcon so that Starship will be nothing like as limited. We can see some of what they are planning from thousands of miles away: land the booster on the launch platform so it is ready to go again promptly and build a rocket garden full of second stages because the time taken to get a second stage back is limited by the slow rotation of the Earth. Next comes the cost of a large number of launches: NASA doesn't care. They pay the same whether it takes 5 or 50 tanker launches. It is SpaceX's problem. Launching an extra Falcon 9 costs SpaceX about $20M. The equivalent for Starship is currently unknown but guesses range from $2M to $10M. Taking the highest cost and multiplying it by a large number of tanker launches (20) and then multiply by the three HLS landings in the contract only gets you to 20% of the contract value. The number of tanker launches does change every few months. So does the lifting capacity of Starship. Falcon 9 payload to LEO has more than doubled since the first version. It is reasonable to expect the same or better from Starship.
Much of what gets Destin worked up on this issue comes from a comparison of cultures. Starship HLS is a firm fixed price contract. SpaceX has the freedom and incentive to find the most cost effective solution. They will do this by experiment and iteration because they need cheap rapid launch for their own business needs. SLS is cost plus. It was designed and simulated to death before being built. Any possible change has to justify the enormous cost Boeing will charge to implement it. At best, SLS will launch once every two years and each launch will cost over $4B. There are multiple huge incentives against experimenting to reduce costs.
While I am here I will mention Destin's other biggest issues. Artemis 3 launch date is currently no earlier than September 2026. It has been delayed before and it will be again. It might look like people are taking that launch date seriously when they pour and stack the solid rocket boosters. Once poured SRB segments have a (theoretically) limited life span. Delays for Artemis I set a new experimental limit. Once stacked SRB's are expected to last a year. When that time was exceeded for Artemis I the SRB's were inspected regularly and found to be still usable. The OIG points out that next time US tax payers might not be so lucky. The entire rocket would need to be de-stacked and the SRB's allocated to the next mission would be brought forward. Boeing would invoice for an extra pair of SRBs, NASA would take the bill to congress who would be waiting with a cheque ready - remember this is a preferred contractor so NASA will not have to piss and whine like they did to get funding for space suits that will work on the Moon.
Next up Destin advocates for the minimum simple solution to achieve the mission. Different groups have different ideas about what the mission is. I think Destin is going for flags and footprint 2. That matches his Apollo 6, Artemis 0 score card. Congresses score card is more like Apollo $25B, SLS $55B so far showing that by their mission criteria SLS is already a winner. For space enthusiasts a more common goal would be to improve technology to the point where a regular shuttle service to a Moon base becomes affordable.
Finally Destin points at the size of the steps between Artemis missions:
1) Orion without life support goes around the Moon and comes back.
2) Orion with a crew goes around the Moon and comes back.
3) Starship launches a propellant depot then N x tanker launches to fill it then an HLS that fills up from the tanker, goes to NRHO and waits for up to three months for an SLS to deliver an Orion with crew. Crew transfers to the HLS, takes a return trip to the Moon then returns to Earth in the Orion.
Destin's talk predates the OIG report on Artemis 1. Artemis 1 had sufficient issues that progressing straight to 2 is now more controversial. He really had an issue with the huge leap from 2 to 3. What the talk does not show is the steps inside the HLS contract. HLS has to get through several milestones (pay days) including an uncrewed landing on the Moon before getting to Artemis 3. Although not in the original contract, SpaceX will also try an uncrewed ascent from the Moon. There is now talk about testing the Orion+Starship docking in LEO. It would be cool if that talk was caused by Destin's video. More likely it comes from a "What if we cannot fix Orion's heat shield soon? We got all this money we have to spend on SLS. How can we get the best value from spending it?"