I fail to see why you need to go to such lengths to 'understand' him,
I just enjoy the music for what it is and appreciate the lyrical genius the man was blessed
with when it comes to songwriting, figuring out what hidden meanings the songs have
is for music magazines and the like imo, songs mean different things to different people
and when it comes to Dylan, much like the Beatles his music was and still is appreciated by folk of all ages.
I'm not trying to 'understand' him as such, or trying to uncover some secret message. I love Dylan's voice by itself, the aesthetic quality of Dylan's music is what engages his fans in the first place, not merely the quality of his verbal dexterity. However, by dissecting and analysing what is, in many, or most of his songs, Dylan's extremely complex songwriting techniques and the imagery presented, as well the way they are performed, one is able to appreciate his art much more. Some songs have simple messages or themes, and do not need to be explained, such as 'I'll Remember You', 'Emotionally Yours' and 'Lay Lady Lay'. All lovely songs, very enjoyable indeed, but no further analysis is needed. Conversely, songs like 'Desolation Row', 'Tangled Up in Blue', and 'Chimes of Freedom' for example, are thematically ambigious, and with a level of analysis can be understood on a different level, and therefore enjoyed on a different level.
It is in the same way as poetry can be understood and appreciated on different levels. 'Daffodils' by Wordsworth, for example, is a lovely poem in aesthetic terms, but when further analysed in terms of the syntax and the poetic devices used by the poet, as well as the context of the poem, it can be enjoyed or rather, appreciated on those terms too. In essence, it gives the poem a greater depth for the reader, and the experience for the reader is more valuable, if that doesn't sound too pretentious!
Also, understanding and analysing what is sometimes pejoratively described as 'pop music' is relatively new. People don't really read poetry anymore, and as such 'pop' music is the 'new poetry', modern balladry. So people are much better versed in analysing poetry and prose, and lyrical analysis of modern music is dismissed. Yet there is as much value in analysing the art of say, Bob Dylan, amongst others of course (Leonard Cohen is another fine example) as there is in analysing Wordsworth, Pope, Keats, Shelley or Byron, say.