When I read this question it sounded like a question I had when I first got into ripping DVDs. After researching interfaces I settled on OGMRip as I didn't want all the bells and whistles that other rippers like dvd::rip offers. I also found myself needing to get a better understanding of video recording and playback such as interlacing and progressive. I qualify this by saying this was self study up to the point where I was able to successfully rip DVDs 95% of the time so if I misuse terminology you were warned. I should also say that this is for NTSC DVDs.
With the option "Ensure A/V Synchronization" checked in OGMRip and an understanding of how the DVD was created I've not had many issues. The only trouble I get is from the not so well mastered workout videos which are interlaced. I have two such videos and both had audio synchronization issues. I was able to fix one by going into the Matroska video container I created and set a delay, the other I just haven't gotten around to messing with yet. One other issue I'll run into with OGMRip is if the DVD isn't quite right it will fail ripping it prior to encoding. For this I just use dvdbackup (dvdbackup -M -i
The one URL I strongly suggest looking at is http://www.mplayerhq.hu/DOCS/HTML/en/menc-feat-telecine.html#menc-feat-telecine-ident as it briefly explains the various ways a video is originally recorded and the DVD mastered along with how to determine this with your video. With most popular DVDs released today they are typically progressive and so when it comes time to rip it I pick how I want it encoded and then check progressive and away it goes. When encoding I use a matroska container, keep the original audio, use x264 for video, and based on the length of the video the rule of thumb of 700MB per hour (increasing if I'm pulling several audio tracks). For your portable player these are probably not the settings you would use.
So the point I'm wanting to make is having the basic understanding of the entire process from recording to the final encoding is what will make any one of the tools work for you. You can then decide how much control you want in the ripping/encoding process. For me the end product is what I want, something I can stream to my TV, not the joy some get spending lots of time getting all the options set for each DVD.
The biggest mistake you can make is to believe that you are working for someone else.