In regard to Ian and Anisa being poor I think
@Incecticyder made a good point. It's not CC flopping that will really kill them (unless they really do get fucked down the line for it, but idk) but the complete slow-down of income and frivolous spending. The amount they overpaid on their house because Anisa apparently insisted on them needing it then and there before CC2 (or CC1 I might be forgetting) is one such frivolous thing. Especially if that reddit post that was going around was real that said the house was in a shitty location and had bad acoustics. The amount of stank and dilapidation they inflicted on the house is also going to affect what they can realistically get for it, which means it can't even be justified as a purchase.
I know Ian has investments and is or was apparently renting at least one property, but how long can this realistically last in the wake of his and Anisa's god awful decisions? I think they're broke mainly in the sense that their big cash cow and creative enterprise is essentially killed now. And they can't exactly live off of Ian's Youtube "success" anymore since it's been similarly killed in a self-inflicted driveby. Maybe they can stay afloat if Ian starts cranking out more shit-tier videos that get less than a million views, but I have a feeling they are circling the drain in terms of their livelihood and comforts.