Sorry for my english, since it's not my native language (I'm from Serbia, but did learn it in school while younger). Anyway, i think Dylan makes an obvious attempt in this one (he even changes for it) to sing from a perspective of a "poor soul"- what i mean is someone who is like a tramp, or a poor musician in old times, like street/brothel player on a certain instrument. Also someone who has been mistreated on numerous occasions and seen it happen to others too, so he kinda "plays it safe" (i'm not talking emotionally, but overall and especially in literal way, roughened up or however you wanna call it, he's on the bottom ladder of society like a tramp, or beggar). Though again i think he states or at least implies in the song he's a musician, so tramp/beggar are just examples.
The Rose Marry is the main focus of narrator's story, she's the woman(and also a place) he's most likely having relations with and who definitely gives him food for work also. That much we can tell from the song. I don't think there's any implications about him being criminal or engaging is such activity. Only verse that could be interpreted that he may have been used for criminal activity and got the fat end of the stick (but definitely not a successful criminal, and not living that life except maybe that thing in the past) is:
Now, if someone offers me a joke
I just say no thanks.
I try to tell it like it is
And keep away from pranks.
But, even this is a far-fetch from my perspective. I think this one is more abstract or metaphorical vision. Joke is kind of a risky social contract type of thing. When someone "offers you a joke", it means that, like it or not, you're gonna have to go along with it and laugh at the end. That's why this can be, among others, be interpreted as a short criminal past, but i think it's not, and what it is, is another example of him being hurt and mistreated and being in the lower corner by society's view. There are multiple examples of him talking about how food is hard to get, even though he's not complaining. As for soft-gut, i think it's just the way men sometimes use words to pet some women they like or love, even though they can be compliments, they can be also derogatory terms or however you call it, on surface offensive but actually a pet-nickname. Soft-gut could also just be some old-term men used for women (if men are "muscles" or "six-packs", women are "soft-gut"; though he's clearly talking about specific soft-gut/fat-gut, it's a women he has that nickname for, or adjective he uses when talking about her.
So tl;dr in conclusion- 1-It's a song about a poor musician who earns his living by playing in a brothel (among other places) and also has a woman with whom he's in relationship there. He's a "poor soul" not living the high life, he's been mistreated plenty, but he's happy when he goes to Rose Marry.
2-As for other comments, i don't see an indication of either A- that he's a criminal or B-that there is 2 perspectives in the song, it's all 1 guy, and all we learn about Rose Marry is that she treats him fair and that
"Rose Marie, she likes to go to big places
And just set there waitin' for me to come."- w/e that part means, i have no idea, but i'm guessing she says she would love to move to some big city, and live the high life, but even though she's not aware she, just as him, is content with things the way they are aka 2 of them having each other to ease the harsh reality.
Sorry for my english, since it's not my native language (I'm from Serbia, but did learn it in school while younger). Anyway, i think Dylan makes an obvious attempt in this one (he even changes for it) to sing from a perspective of a "poor soul"- what i mean is someone who is like a tramp, or a poor musician in old times, like street/brothel player on a certain instrument. Also someone who has been mistreated on numerous occasions and seen it happen to others too, so he kinda "plays it safe" (i'm not talking emotionally, but overall and especially in literal way, roughened up or however you wanna call it, he's on the bottom ladder of society like a tramp, or beggar). Though again i think he states or at least implies in the song he's a musician, so tramp/beggar are just examples. The Rose Marry is the main focus of narrator's story, she's the woman(and also a place) he's most likely having relations with and who definitely gives him food for work also. That much we can tell from the song. I don't think there's any implications about him being criminal or engaging is such activity. Only verse that could be interpreted that he may have been used for criminal activity and got the fat end of the stick (but definitely not a successful criminal, and not living that life except maybe that thing in the past) is: Now, if someone offers me a joke I just say no thanks. I try to tell it like it is And keep away from pranks. But, even this is a far-fetch from my perspective. I think this one is more abstract or metaphorical vision. Joke is kind of a risky social contract type of thing. When someone "offers you a joke", it means that, like it or not, you're gonna have to go along with it and laugh at the end. That's why this can be, among others, be interpreted as a short criminal past, but i think it's not, and what it is, is another example of him being hurt and mistreated and being in the lower corner by society's view. There are multiple examples of him talking about how food is hard to get, even though he's not complaining. As for soft-gut, i think it's just the way men sometimes use words to pet some women they like or love, even though they can be compliments, they can be also derogatory terms or however you call it, on surface offensive but actually a pet-nickname. Soft-gut could also just be some old-term men used for women (if men are "muscles" or "six-packs", women are "soft-gut"; though he's clearly talking about specific soft-gut/fat-gut, it's a women he has that nickname for, or adjective he uses when talking about her. So tl;dr in conclusion- 1-It's a song about a poor musician who earns his living by playing in a brothel (among other places) and also has a woman with whom he's in relationship there. He's a "poor soul" not living the high life, he's been mistreated plenty, but he's happy when he goes to Rose Marry. 2-As for other comments, i don't see an indication of either A- that he's a criminal or B-that there is 2 perspectives in the song, it's all 1 guy, and all we learn about Rose Marry is that she treats him fair and that "Rose Marie, she likes to go to big places And just set there waitin' for me to come."- w/e that part means, i have no idea, but i'm guessing she says she would love to move to some big city, and live the high life, but even though she's not aware she, just as him, is content with things the way they are aka 2 of them having each other to ease the harsh reality.