The Squeezebox Touch allows you to attach a USB storage device like a thumb drive or hard drive, without any other interface. The larger the library, the longer it will take to cataglogue via the Touch. I have not tried this with a larger hard drive, but it worked like a charm with a thumb drive with FLAC files on it. I believe that if you do use a hard drive it needs to be formatted in FAT16 FAT32 NTFS or ext2/ext3. If you are not computer savvy that may not be a simple solution, but it does eliminate the need for a computer interface (I actually still prefer to use one because control is more comprehensive via Squeezeserver on a laptop). You'd still need a computer interface to rip the files in the first place, of course.
itunes probably provides the most user-friendly interface for ripping, cataloguing, and playing music, but alas, it does have some drawbacks. The ripping component is not as vigorous as some other software - you mentioned Media Monkey, there's also EAC and Max (if you are using a Mac) that come to mind. Any one of those have a better error-correction built in than the one in iTunes. Also iTunes can not handle FLAC files, which I prefer to use, and also is a bit awkward in handling hi-rez audio files which require adjustment of the MIDI interface as opposed to adapting on the fly to whatever you choose to play (again, non computer-savvy need not apply here). If you do use iTunes I would rip files in AIFF or Apple Lossless (the latter taking up less space). Do not use WAV files or you may regret it down the road.
