Sorry, but as a challenge for myself any hints that I give would be in the form of a drawing. Except for high level meta hints.

If no one guesses I'll post more pictures.

So what about drawing the MS-DOS logo if it is DOS ;-)

Ha, no.
But since you asked, here is hint 2 :)

I have a feeling that I have seen it somewhere but I can’t remember where...

Is it a Tintin game?

No.
I'm not sure how to continue... I could draw more screenshots, but to be honest, unless I draw them with complete accuracy, which given my paint skills is impossible, if you didn't recognize it from no. 2 you're not likely to recognize it from those either.
I think anyone who played the game should have recognized #2. It's the main menu, you can play a random game by clicking on the globe, a historical scenario by clicking on the book, connect to multiplayer by clicking on the phone, or host your own multiplayer using the quill and ink. If you've played before, you can load a game from the ship in a bottle or view your highscores from the medals display. And if you want to exit, there's the door.

And given my rules about drawn hints only, I can't even tell you that the game is not a DOS game but was released when DOS games were still being made.

Here is the final attempt. If no one guesses, I'll just pass my turn.

EDIT: Well, after drawing it, I can't imagine how it's going to be helpful for someone who hasn't guessed it from the previous 2 hints. But maybe at least the genre will become obvious.

Shoot, I forgot one dude.

I don't know what it is, but it reminds me of a RTS game from what I believe to be the early 2000s.
Unfortunately I can't remember the name or much about it.
All I remember is a humvee-like unit and I think you ran like a private military company.
I don't remember any cowboy units though.

No. It's not that.

Don't pass yet. I will be back from my vacations today so I'll have some time to think about it

Well, one more thing, the forester dude should have an axe instead of a saw. But I didn't want to make him look like a warrior.

I still think I know it but I've checked a few games but they don’t match your description so I won't guess it

I'm going to give the answer and ask someone else to take my turn then.

The game in question is Imperialism. The first image is from the game's box, the second is the main menu
http://www.mobygames.com/game/imperialism/cover-art
http://www.mobygames.com/game/windows/imperialism/screenshots/gameShotId,13264/

The third are the civilian units in the game.

It truly is one of the best turn based strategy games I've ever played, and I'm not saying this lightly.

It's a bit of a hidden gem, so if you enjoy turn-based strategies, do give this a try. You can get it really cheap on sales if you don't want to pay the full price.

Shame on me! I knew the game after all...