Hello, and welcome to CF.
"Gambling" could be extended to many things, even more than you've outlined. In many cases just trying to do a thing, challenging ourselves, is a gamble. On the other hand, if you define gambling as necessarily involving money, then starting a new business, advertising, and investing are all gambling, in a way.
I don't think it's gambling, per se, that is the problem. I think it is the result, and that's going to vary depending on persons.
I hate casinos, unless I can play pennies, because my money is too hard-won to throw away. I did enjoy a "casino" one time in a place where gambling was illegal, and you just played with special chips they gave you, no cashing out or prizes to be won, and nothing lost either. And I used to go to the racetrack. I learned to read forms and horses, and I'm actually very good at picking winners (we lived near a track and half the family worked with either the track or a nearby farm). But I so hate to lose money, that I would either pick them and not bet, or else bet low and safely so that I didn't win much. Gambling is no thrill at all to me, it's an anxiety, even though I know I can almost always win.
I say all that to say, gambling is probably "not a sin" for me, for that reason. I'm not pulled in by it, and I won't do anything irresponsible.
It comes to mind that this may be very like drinking alcohol. Drinking alcohol is not a sin. However, getting drunk and doing sinful things, getting drunk habitually, wasting ourselves for alcohol, ruining our health with it, hurting others because of our drinking - all of these are sinful. Some people who drink will almost certainly end up doing these things, so for them, any drinking might be sinful. Others cross a line somewhere, and then it becomes a sin.
I think many things are not sinful in themselves, but what comes out of it can be a sin. So it's not so easy to answer your question - it might depend on the person too.
I won't try to answer for you, but since I explained myself a little above, I'll answer for me, in MY personal makeup and tendencies.
1 - not a sin in my case (though I would do this without the money just because if I'm not sure, I don't want to lose, and if I am sure, I don't want to create any hard feelings by taking it from the other person - in fun I could imagine myself maybe betting some little chore or trinket, if I know no hard feelings will result)
2 - not a sin in my case, as I said I've done a "casino" where there was no actual winning/losing, so I'm thinking of that
3 - I simply can't imagine that because it would ruin the game for me, worrying about losing, not make it more exciting. For me, any motive (I can't imagine one) that might make me do that in the way you describe probably would be sinful, because it would involve wrong motive. For me.
4 - would depend. I'd be foolish, lol, casino gambling is overall a losing game of odds. I could have made money on the horses, because I'm good at it, and I did consider it for a moment. But yes, it begins to get into motive. In my case, only greed would push me there I suppose, and yes, that would be a sin.
Like I said, I answered for me, mainly to illustrate what I mean by "it depends". Your answers may be - and probably are - quite different, but I can't judge you based on the little you have shared to offer an answer.
Is gambling wrong in any situation?
No, unless you want to say challenging ourselves or investing are wrong. But gambling (as in gaming with money) is probably wrong in more situations than just gambling (as in taking a chance) would be.
Is gambling wrong based on with what intentions you do it? (fun vs. greed)
This is certainly a very important factor to consider - one of the prime ones, along with the others you listed below. Doing anything out of greed is wrong, because greed is wrong. (The love of money is the root of all evil.)
Is gambling wrong because it is very addictive?
It depends on the person. As I said, I'm pretty impervious to becoming addicted to gambling, so in my case, no. I am not sure if it can make an addict of someone not already inclined, ever (in my case I think not - other things can draw me in an addictive way, but not this). But for someone easily drawn into it to the point where they do anything foolish, then it is definitely a sin for that person.
Is gambling wrong because it is fuels greed and other finance related evil?
Possibly. It is worth looking at the whole picture. People get upset over farming practices of cocoa that take unfair advantage of workers, and rightly so. I don't even like to think of what the "gambling industry" may be connected to. So you have to ask if you're supporting evil. And you probably meant on a personal level, fueling greed in ourselves? Again, if it does that, it is most definitely a sin, and very damaging to our spiritual health.
How's that for a very long-winded not-really-answer?

But like many things, it does depend. All things may be legal to us, but not all things are profitable. We ought to seek that which is good and beneficial for our souls.
Again, welcome to CF.