When Korolyov worked on N-1 rocket in 1960-s, some plans included building a hydrogen upper stage. http://astronautix.com/n/n1blocksr.html Hydrogen is rather hard to keep cold, but that stage was designed to work for over 11 days.

Falcon-9 flies almost every other day, about 3 times per week. Methane is way more storable than hydrogen. Of course we'd like to compare numbers, but, given that Starship is way bigger than than N-1 stage - about 15 times, and there is the law of squares-cubes, which for our case says the bigger the tank the less percent of boiloff per unit of time, and it's methane, and we can afford to lose a little and top off with another tanker...

Now, how many tanker flights we'll need? That's a favorite riddle in Musk's plans :) . Korolyov, again, had some early ideas for 5 tankers - https://graphicsnickstevens.substack.com/p/sever-the-bridge-... ... For Starship - if you have 1500 tons of fuel in the Starship, and 150 tons of payload in a tanker, you need 10 flights. You can probably optimize, or be disadvantaged by some obstacles - so, 8-12 flights? That many can fly in less than a month. We can also use additional measures to reduce boiloff - better protection from the Sun, active cooling, maybe more permanent orbital refueling depot - but still, with our today's Falcon-9 flight rate we may consider one Starship per month refueled on LEO. Even if some refueling flights won't be successful, the replacements could be sent.

I personally suspect Starship will fly much more often than Falcon-9. We're so much better in rendezvous and docking these day than we were during Apollo flights, the reliability is so much higher - just take a look how many Falcon-9 flights in a row are successful - so I don't think operationally LEO refuelling will present a significant problem. And I'm sure we need maybe a couple of years to see first examples of that.

Space is hard, yes. But we're getting better, for sure.