Currently I think the game really doesn't want to set you up to failure ... I could see them implementing difficulty levels where on a higher difficulty you do get locked into a part of the game and have to get through it without abusing long rests ...
I'd think it very likely that Larian will implement difficulty settings, and I guess it's possible that rest frequency/cost and stealing skill checks might be configurable as part of that.
I also think you're right that Larian don't want to set us up for failure, and while I'm not a PnP player, I understand that's in the spirit of D&D. And it seems that Larian are very much erring on the side of being a permissive DM, giving players the flexibility to do as much as possible and create the stories they want even if this can be exploited, as opposed prioritising giving us constraints to test ourselves against. We need both, but while they’re not entirely mutually exclusive, they are in tension. And personally I am very sympathetic to a balance that tips towards flexibility, and we can always set our own challenges on top of those actually imposed by the game if we want to. That said, there are some specific cheesy mechanics I desperately hope are changed, but the possibilities of infinite long resting and cash are ones I'm happy to just ignore
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I'd suggest moving further discussion on this point to one of the active existing threads linked to above so we don't end up having overlapping discussions in various places!
