1

Can I use the verb "possess" in describing a person's level of proficiency in some language?

Just like his brother Henry, he possesses some amount of Japanese that enables him to handle simple conversations and express himself more or less correctly.

3

People would understand what you meant but the expression would not be idiomatic.

More natural ways of saying this include:

has some knowledge of..
has some fluency in...
can communicate/converse in...
can make himself understood in...

and, as you say,

can express himself in

2

A somewhat dated idiom is to "have" a language.

We simply cannot hire her. She has no English at all.

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