[General] Each time I watch the video....

[Silverobama]

An old online video moves me. The things there are real. A man whose parents, wife, daughter, older brother passed away in different time in his life. He was once sad but finally decided to move on. I now watch his videos from time to time. Sometimes when I feel discouraged by my life, sometimes by bad things happened to me. Each time I watch the video, I feel encouraged a lot by the man.

Is my italic sentence natural?

 

[Charlie Bernstein]

An old online video moves me. The things there are real. It's by a man whose parents, wife, daughter, and older brother passed away earlier in his life. He was once sad but finally decided to move on. I now watch his video from time to time, sometimes when I feel discouraged by my life, sometimes when bad things happen to me.

Pay attention to parallelism.

Each time I watch the video, I feel encouraged a lot by the man.

Is my italic sentence natural?

Yes, it is. Others here might have other verbs to suggest.

 

[jutfrank]

It's not right to say encouraged a lot. Instead, you can put a modifying degree adverb in the position before encouraged, like this:

Each time I watch the video, I feel greatly encouraged by the man.

However, I'd suggest a different phrasing, such as this:

Each time I watch the video, it gives me (great) encouragement.

This means that it's the act of watching the video that encourages you, rather than the man himself. I think that's close to what you really want to say. Otherwise, you could keep my first suggestion and drop by the man:

Each time I watch the video, I am greatly encouraged.

Notice that I've changed feel to am, but feel is okay there too.