chess playing

a. He is a guitar-playing youngster trying to impress girls.
Could this be used if the meaning is that he is playing the guitar right now?
Could it be used if he isn't playing the guitar right now, but plays the guitar?

b. He is a drinking man.
Could this be used if he is drinking right now, but is not a habitual drinker?

c. I walked into the bar. There was a man sleeping at a table and two men drinking alone at the counter. I talked to a drinking man.
Does this work? The idea is that I talked to one of the men who were drinking.

d. I saw him sitting there in the park across from my cousin, staring at the board. He was a chess-playing five-year-old kid.
Does this mean he was a five-year-old kid who was playing chess at that time or a five-year-old kid who played chess?

Many thanks.

Sentences a, b, d: no. The adjective says he does this (or is this, for d) regularly, not "right now".

Sentence c is unnatural. You can say "I talked to one of the drinking men". Here "drinking" identifies which man you talked to, rather than describing the man.

azz said:

a. He is a guitar-playing youngster trying to impress girls.

I'd say this is possible as a general description, not as a description of what he was doing at that moment.

azz said:

b. He is a drinking man.

I'd understand this as (a slightly old-fashioned sounding way of saying) he drinks regularly.

azz said:

I talked to a drinking man.

I agree this doesn't sound natural in the context.

azz said:

He was a chess-playing five-year-old kid.

Again, this doesn't sound natural in this context. It might possibly work as a general description, with the right backdrop.