What would you look for in Cuba to see the true nature of Communism?

[Balu]

... I plan to dig even deeper to see what life if really like under Communism.

If your goal is to understand what communism is in the ideological sense, Cuba is not the best choice. It is better to choose China, which, unlike Russia, is still a communist country. They both (Cuba and China) have the same 'value scale', but different opportunities to achieve the targets.
Then, for obvious reasons, you will face great difficulties, to learn something. You should understand that there is no flow of tourists to Cuba from the United States and your private visit, to say, from 'unfriendly country', which economically blocked Cuba for decades, might look rather suspicious to the authorities and will not encourage local residents for close and frank contacts.
I would recommend you to think all above over before wasting your money.