And my guess is that once Luke was old enough to manifest Force powers, he didn't even take work - lived off the land or off the grid somehow. And he was a wanted man, he could never be around anyone who might recognize him or mention him to an offworlder. So somehow, he had to be there when Luke needed that push into Jedi-dom, that was his whole purpose in going to that hellhole.
This.
Obi Wan couldn't get a regular job because of the high risk of being recognized, especially during the first years after his arrival on Tatooine, when he was young and hot.
He thought about whoring himself and work as a male prostitute in the corrupt and dark streets of Mos Eisely, but after getting his first prostate exam, he immediately figured anal sex would lead to the dark side of the force as well.
So instead he decided to take care of himself jerking off four times a day thinking of Padme and how he missed that easy chance of raping her in the battle of Mustafar.
Time fles and next thing you knew, he's like 60 years old, still jerking off and living of crabapples and paddy.
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