Jarkeld got it. It was Monkey Island 2

Clue #1: Near limitless possibilities to try to get rich, so very few possibilities that actually make you enough money to live on.

It sounds like a dystopian society. Goin' Downtown?

Unfortunately not.

Clue #2: Advanced technology exists, but we hardly know anything about it: how it's made and even how it works.

A Tex Murphy game ??

No, but it's roughly from the same era

The New Adventures of the Time Machine?

Too new.
Clue 3: Humans wrapped in tons of rock and metal, all alone in the night. Or are they?

Is it Dark Side of the Moon?

Chamber of the Sci-Mutant Priestess?

If its not what Becky said it should be
Very cool name!

Nope.
Clue #4: Your spaceship may know which way to go, but you sure don't

One of the Space Quests?

It sounds like Babylon 5 .... Which would make it a "Darkside" game ??

It's not Space Quest (it's more hardcore SF, based on a book) nor B5.

Clue #5: Despite the name, the main character is definitely male.

Gateway - One of the best sci fi series by Frederik Pohl

Correct! You've got it CountZero!

Clue #1: You know you've had a hard night when you find yourself face down in a plate of
synthetic pasta with a ringing in your ears.

I reckon this is an old infocom game but thats about as far as I get at the moment.

Space Bar?

Clue 2: An assortment of implants for street skills came in handy, from "coptalk" to win over the police in the donut shop to "musicianship" for persuading the Rastafarians on Zion with some good dub music.

Neuromancer?

Correct

Wow, that was a blast from the past. It had been years since I played that game.

Clue#1

Who am I? My "dog" is named Pantagruel.

Clue#2

The bad guy has a pumpkin on his head.