Coming in very late to this discussion. I've only converted commercial dvds (ones I rent and ones I own), but this is what I do:
I bought the paid version of Aimersoft DVD Ripper for my laptop. If I recall correctly, I used the free version at first, and then was happy to get the paid version. I've used it a LOT. I can recommend it without hesitation.
When you get set to rip/convert the DVD, it gives you an extensive menu of devices to rip for. I mean extensive. I, of course, chose the Samsung Galaxy Tab option (I can't remember if it gives you an option for Tab vs Tab 2, but it doesn't matter, see below).
This menu of devices simply shortcuts your need to know what file format is used by your device. If you know that, you can simply tell the program to rip/convert the file from the dvd that particular format. There's nothing magical other than the software knowing what format your device uses.
The Samsung Tab setting rips/converts the file to an MP4 file which is readable on my Tab2 and many other devices. Really, all you need to know is what video file formats the player on your device uses, but I think MP4 is a pretty generic and universally usable format.
As part of the rip/convert menu, you choose the folder on your computer to save the converted file too. It defaults to a file it names in your Documents folder, but you can create a destination file anywhere and tell it to save there.
Then you just hook up your device to the computer - I use USB, I haven't tried wireless for this. You then find the videos or movies folder on your device or make one on your external SD card. I can't remember what it's called, it might not matter. You simply copy the converted files from your computer to the device in the proper folder.
I mention it might not matter what the folder is called, because -again if I recall correctly - your video player app on the device will search for video files when you open it. I'm a little vague on this because it's become so routine for me. But I don't recall any real problems the first time, except for maybe figuring out exactly where to put the file on the device.
There's easy to follow user interfaces on the Aimersoft ripper. One thing that I played around with was exactly which files on the DVD needed to be copied. The software automatically chooses the main movie file which is the complete movie beginning to end. That is pretty fool proof. There's a bunch of other files on the disk, separate files for some opening titles, movie pre-views, extra features, etc. I generally convert and transfer all the files, but put the minor files into a separate folder within the video (or movie) folder called something like "extra files". Then when I'm bored on the airplane and the movie's done, I can look at them and see if there's anything interesting I missed, like the outtakes, previews etc. you can generally tell which files are of possible value by the size. You can also preview them within the conversion screen before you actually rip them if you want.
Hope that is germane to your question!