What is the difference between Wine, Wineskin, Winery and Wine Bottler, and how do I get Wine to *ACTUALLY* work in Mountain Lion?

Ok, so this is my first post here and I am admittedly terrible at forums. Someone might say, "This was addressed in the ___________ thread by __________! Go read it!" --- that may be so but I've spent enough hours trying to google this problem into submission to no avail based on what is apparently working for others, so I would like a chance to get specific answers to specific questions that aren't from Mar 2011, etc.

So first of all, I'm confused by all the various Wine programs/apps/whatevers. I've seen Wine, Wineskin, Winery, Wine Bottler, and at this point I wouldn't be surprised if there are even more than that. What's the difference between all of these and how do they work with one another? What do I actually need to get windows programs working?

All of my google searches have led me to people giving out fish, but no one giving out fishing lessons. I'm not a pro at mac and windows and all that, but I'm a fairly bright individual who gets VERY frustrated, very quickly, when I don't understand the why and how of something I'm attempting.

I've also found "answers" where the person attempting to help starts off helpful enough, but degrades into the most archaic of techno-babble after about 5-6 sentences. On the other hand, I've watched tutorials on youtube where the poster decides to skip (apparently crucial) sections of the tutorial, and mutters such gems as: "... you might wanna have to run Wine first before you can do anything, cuz I think it has to configure it and set up a bunch of stuff"

O.o

A happy medium between techno-babble and the most basic of explanations would be ideal for me, and I'd imagine for others as well.

Here is a summarized history of my relationship with Wine:

Diablo II - I downloaded this awesome thing which ended up being... uh... I guess Diablo II in a Wineskin "wrapper". I'm not sure, all I know is that it's a D2 icon, and if I go to 'show package contents', it's got C drive, Program Files, et cetera inside of it. I double click it, it launches D2, and it works like a dream. <3

'Vanilla Install' - That's what I heard someone call it. It was the command/terminal style install using xquartz and xcode found at http://www.davidbaumgold.com/tutorials/wine-mac/. I followed every instruction to the letter, and got all the way to '$ sudo port install wine', at which point it started going smoothly, free from the possible error he described regarding the installation of xcode, and then just failed after I left the room to use the restroom and came back. Please don't ask me to repeat what the error was, because honestly, after reading more things on the interwebs, I'm confused as to why it's even necessary to go through all of that, so I'd rather not try that route again anyways, rendering the error message quite possibly irrelevant.

Wine + Wine Bottler - So I decided to try to seek out an easier method, as I know that one must exist that doesn't involve command lines. I found a video tutorial at http://www.youtube.com/watch?v=m0BBkISOcEA, and oh man would it be great if that method had actually worked. Again, I followed all instructions provided to procure my free fish, and at the point in the video where he declares that "xquarts or x11 will open" - it doesn't open. Nothing opens. I was trying to install Star Sonata, btw.

So here I am, thoroughly worn out, frustrated at all the random places Wine is installed on my mac now, and just want someone to explain it all, from top down, without getting toooooooo technical on me. I know that might be asking a lot...