Mark’s Down On Your Syntax said:
TESB spans several months, almost a year.
I’d say a few weeks at most.
Could you both give more details about how you see the time passing? What makes one of you feel like it’s months and the other just weeks? This is really interesting.
In my head canon, the Millennium Falcon's trip from Hoth to Bespin took several months travelling at sublight speeds. Time dilation kept the crew from experiencing that amount of time, so that’s why they didn’t arrive starved/dehydrated/really grungy. Luke spent that same amount of time on Dagobah training with Yoda, explaining his advanced Force/lightsaber duelling capabilities and his “I learned so much since then” bit of dialogue.
The two things that take a while are the trip to Bespin and Luke’s training. The longer the flight takes the longer Luke gets to train. At minimum the trip to Bespin will take weeks. It more likely takes months or years depending on the distance between systems. If we are generous with the Falcon’s speed and the distance between systems, I would say 1-2 months. The story allows for that. The Falcon likely has bathing facilities and could easily carry spare clothing. Han and Chewy live on it after all. That gives Yoda a fair amount of time to cram in a decade of training. Luke obviously retained most of it because when he comes back Yoda says he has learned enough. That would be impossible in a week and super tough in a month.