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This is the first update where you get to pay 100 GTA$ per day just to own a regular 10 car garage.
But to answer the first question... it depends on the kind of player you are. Owning a penthouse gets you full access to the casino (you could also buy a guest day pass for 500 GTA$) so that you can gamble.
The penthouse itself is sorta fun but also nothing new. Basically you can buy extensions ("modules") which add already existing stuff to your penthouse. So: you can get a barber, a hot tub, a bar & bartender, a cinema and all that in your penthouse. Stuff you can also find across Los Santos. And stuff that doesn't really 'do' anything.
What could be fun is having access to the new missions. Payout is mediocre to plain out bad but some missions can be fun to play, I'm enjoying the "VIP missions" so far.