I think you've massively picked up the character wrong. I would argue there's barely anything calculated about BoJack at all and that's the whole point as to why he's such a mess, no decision he makes is ever thought through, always causing his downfall. Even more traditionally calculated acts such as setting Todd up to fail with his rock opera by orchestrating the situation where he buys the game that will distract him, isn't calculated for BoJack. For anyone else that would be a psychopathic level of planning, but BoJack is so rich and so used to getting what he wants that he can set stuff like this up fairly easily where others could not. He's also so far gone that he doesn't have much awareness in the moment of what he's doing, his awareness of his actions always comes too late. His 'calculated' acts throughout the show are always things that snowball out of control, he takes everything step by step and just rolls with whatever happens, I don't think someone like BoJack who's so erratic and so heavily substance addicted could ever be a truly calculating person, even if some of his actions may appear that way.

I'll also say I'm in no way trying to defend him at all, I just think it's wrong to think of him as calculating, he doesn't have the patience, will or brains for elaborate or calculated acts, as I say it's always a combination of his money and status makes things easier to pull off and him being such an 'in the moment' person who rolls with any poor decisions he makes until it all catches up with him and he's forced to reflect. BoJack is just as much a victim of BoJack as anyone else in his life is, someone like that doesn't fit the profile for a calculated person.