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.
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.