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I was considering buying a mallsai (I know shoot me) of a Hawaiian Umbrella. I was wanting to know if I kept it outside during the warm days and nights and brought inside for the cold times how long and how difficult would it be to go from the first picture to the second picture

20 years, very difficult if not impossible.

depends on where you live.
In the tropics, you could reach this within a few years. In temperate zone.. A lifetime?
Just out of curiosity.. Why would you even want to try? It is not like the second picture shows an interesting bonsai?

Instead of focusing on an end goal, when you haven't even bought a tree, you should buy a bonsai and see how you should style the tree. Copying isn't art and you should make a bonsai that is from your own artistic standpoint. But, if you still would like to make a similar design as the second picture, I would say how old is the tree you are buying and where do you live?

It is not like the second picture shows an interesting bonsai?

Leatherback is correct in the sense it isn't the most beautiful bonsai you could make that tree.