Not sure if anyone else had a theory like this but I had a talk a long while back with a friend.
It wasn't directly related but we came to a moment where we discussed Larry's living situation.
Mainly that he was a job hopper until he decided to focus entirely on an art based career, which is notoriously not really profitable if until you get a proper takeoff.
But he didn't seem to talk about his living situation much? Or, more specifically, that he was financially suffering or anything. There is no mention of that. Unlike Phoenix when it's often a big joke that he couldn't afford rent despite being a successful lawyer, one of the most high profiting jobs in most modernized countries.
Now obviously it was to make the unreasonable "haha Larry sucks at art" joke rather than a starving artist joke but I actually have a theory regarding to that in context with everything else:
Larry comes from old money.
Think about it, his behavior and general demeanor in regards to money is very flippant and almost nonexistant. Like yeah he stole money as a kid, but kids are dumb and will do whatever they want.
But his goal wasn't money as he grew up. It was finding a relationship he can stick with. This also explains why he was able to bag hotties but never able to keep them. Or at least the first part is explained.
The second part, I think, is because he is fairly independent and doesn't use the money he grew up with on lavish gifts or big surprises. Instead, he earnestly made every gift himself as he was an aspiring artist ever since we got introduced to him (remember? The Thinker was made by Larry!).
This, of course, led to girls who came for the money leave because he wasn't a spoiled rich kid. Rather, he was an earnest guy who lost because his life was too lucky.
And no, I do not accept the idea he was bitchy to his girlfriends, he was always complimentary about them and he is very sweet to the women he likes.
Anyway these were some 2 am ramblings from cle. Goodnight <3