I can help you with some of these with certainy and "educated guesses" on others. An "educated guess" is likely to be correct because it is based on a person's knowledge of the context.
1. I've never heard this one before, and I've lived in several different regions of the United States. This is a paradoxical statement. Two situations which we would normally not think of as being able to exist at the same time, do. I think it means that the speaker "I" is showing gratitude to someone for whom he in turn is responsible in helping to achieve great success. I can imagine people in close relationships, such as husband-wife, mentor-protege, a leader--followers, even an older parent--adult child, using this phrase to thank one another for creating a foundation of success that later allowed him or her to "make" the other person successful.
2. This is a fairly common phrase, but I don't hear it very often from my students. I'm not sure of its exact origin. There are many superstitions about odd numbers and inconsistencies, left-handedness, etc. Historically, people don't like things that don't appear even, routine, common, and symmetrical. Anyhow, "to be at odds with someone" means you are in a [U]state[U] of disagreement and mild conflict with that person. You don't enjoy being around each other, but you are not openly violent with each other.
3. A person described as a "Goody Two Shoes" is being criticized for being too prim, too proper, or too prissy and for following rules so closely that by comparison others' efforts look bad. Also, very often, a "Goody Two Shoes" is suspected of giving a false appearance and impression following rules so perfectly, of being a hypocrite by acting one way and publically professing one set of beliefs, when privately he or she uses that image for his or her own purposes. This is very common in use from people of my grandparents' generation up through my own (1890's--1960's), but very few of my students (who are teenagers) use this expression.
4. I don't know this one at all, but I'd guess that it's recent hip hop/rap slang and one of those catch phrases that people will drop into a conversation as part of the flow and overall interaction with friends. Have you noticed that when a small group of friends are talking, who have known each other long enough to have shared experiences, that the way they stand and the distance from each other, as well their gestures and expressions, can be as important parts of the conversation overall as the words that are actually spoken? People who share some similarity, such as being of the same generation, having the same interest, or living in a particular location, will recognize a phrase like this because it's from their shared source, and whenever they use it, it's part of the fun and bonding.
5. I love Looney Tune cartoons, so I can answer this question authoritatively. In the Bugs Bunny cartoons, Elmer Fudd is the hunter whose pursuit of Bugs always ends disastrously--for Elmer. He has a speech defect, and in the 60+ years of the cartoons, he's always drawn as some variation of an old-fashioned gentleman who is easily confused and enraged when he realizes he's the victim of Bugs' jokes. Bugs Bunny always asks, "What's up, doc?" With his speech impediment, Elmer's reply always sounds like, "I'm hunting wabbits." For the rest of the cartoon, Bugs, the trickster rabbit, will put Elmer in increasingly ridiculous situations as he often "helps" Elmer hunt him. No wonder Elmer Fudd is confused, stutters, and can't pronounce "R" sounds.
6. I've never heard anyone say this, but it's funny. I'd interpret it to generally be a humorous rhetorical question. The speaker isn't actually expecting a reply to his question and isn't asking about vacation plans on the Disney Cruise Ship Line. It's a small joke asking if a friend is daydreaming, or letting his mind wander. Disney films are mainly magical fantasies and cartoons, so if someone is "cruising Disney" perhaps he has let his mind drift from the real world of the moment to a world of hopes and wishes.
7. This is an extremely common expression and has some slight shades of meaning because it can be used in many different situations, but they all convey a meeting, a coming togehter, under casual circumstances, on impulse, or because of convenience. For example, a mother with two small children leaves her home under ordinary circumstances, such as going to a grocery store, and on an impulse decides to pick up a prescription at the pharmacy and drop off the laptop computer she was repairing for a friend while she is "out and about." It is easier to do all of these tasks now instead of waiting until later after she has returned home when it may not be convenient to make another trip.
8. "It was not a winning way to say it" is a gentle form of criticism. Instead of stating, "Your phrasing made your point but failed to achieve your goal," the speaker shifts some of the emotional hurt and blame one might feel by saying, "you did not win the results you wanted," rather than, "you failed, you offended others."
Hope I helped!
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