I'm not aware of any one source that compares and guides one this stuff. Maybe Assassin did something. With that said, if you literally have hundreds of disc to rip, it's going to take time. How much time is going to be dependent on your machine, especially the CPU since ripping and transcoding is CPU intense.
Assuming you want to convert your discs to mkv, which I suggest because it's becoming more and more popular everyday, I would start with MakeMKV. This program literally just takes the discs and converts to a mkv container. So, your blu ray disc will be about 20GB versus the 25GB, and DVD will be about 4GB versus 8GB. If you have a lot of space and want highest quality, stop here. I'm not aware of MakeMKV haven't a que for jobs, so it's just one disc at a time. In addition, doing this first, will save your optical drive if your proceed to the next step, which will be using it, potentially, for hours.
If you don't have a lot of space or you don't want to use that much space or willing to sacrifice some quality, this is where Handbrake comes in. Take your MakeMKV file for the source, set the Handbrake to mkv, pick your favorite settings, and transcode away. For most, normal will be sufficient. For those a little more decerning, High Profile will be adequate. Just make sure to include subtitles in both MakeMKV and here. For handbrake, check the default so it will automatically trigger when a foreign language is spoken. I like to include chapters too so it makes it easier to skip around. For audio, I just use autopass through. This gets take my 20GB mkv rip and shrinks it to about 4-7GB. The rips are not absolutely perfect, but just as good, if not better from Netflix's 1080p HD feeds. Since I have eye issues, the biggest difference the original disc is just crispness. The bonus to Handbrake, it has a que. So you can create a job listing to convert the MakeMKV files. Again, how long this takes is very CPU intense. I'm on a just dual core machine, so it takes about eight hours per blu ray. In MakeMKV, and blu ray takes about forty minutes. I've read if you have 8GB ram and a eight core machine, it's about an hour, maybe less.
I also use AnyDVD HD too. For MakeMKV, they say to shut it off because it could cause issues. I haven't run into any issues as of yet. Sometimes MakeMKV is unable to break the encryption, but AnyDVD does. Either way, the rip from MakeMKV will be encrypted free, so Handbrake will not need AnyDVD. There two programs are the most popular.
Your other question is really about how best to playback these rips. This is really going to depend on the experience you want. I would recommend Plex or XBMC. Another factor will be the devices your plan to playback your media with. I personally use Plex. Plex is an excellent choice if you want to access to your content outside of the home. XBMC is working on this too and has a working version, but Plex is significantly farther along and polished. I haven't used XBMC in over a year, but the player on the PC was better than Plex's. Plex has improved the player a lot. I just don't know how it current compares. Both are going to give similar front end experience with metadata, menus, and so forth.
The one thing I like about Plex over XBMC is the server and front end setup. Once the PMS setup, all your doing is adding front end clients to you devices. There's not needing to point where your content is on each device. I use plex an my android phone and tablet, PC, and roku boxes. And I can even use it on through a web browser.
If you just want to playback, anything like VLC would work.
Unfortunately, I don't know all the options available in OSX. I'm on Windows 7, but use the Mac Mini (late 2009 model). In Windows, there are significantly more options for makemkv playback. And there are other suites other than Plex and XBMC such as Media Browser and Media Center. I'm not sure of it's supported in OSX, but I know Plex and XBMC both support HD audio in Windows.