I have not read the rest of the thread so consider my response in context. I reserve the right to amend my response as I read.
Fucking do it!!!
Probably more than one. You have a great voice and people will want to read you once they find you.
Personally, if I were you, I would start a memoir about bouncing before quitting and road tripping - like now!
Then, while you are travelling, you can work on both. Stephen King described his writing process in his memoir, I suggest you read it. He would revise the older book first, then write the new one once he was warmed up.
That is a simplification - if you want more summary, I am happy to provide.
Bryson is a storyteller and that is why people bought Walk in the Woods. Gotta be honest. Meyer was a good character, but it was the writing and the story that got me, made me want to do the Appalachian Trail, buy the tent, schedule a section hike, buy Snickers.
Glad you have a grasp on this. Most writers starve. Very few can afford to write full time. Of course, self publishing has changed the paradigm, but you might consider writing a few query letters to magazines and publishers to gauge interest.
Fear and Loathing in T-Nation - meet some forum members without the LSD . . . or with, your call.
You could document it on Social Media as you go to build interest.
I’m going to stop quoting and posting - I got a little excited about the idea.
If you get to NorCal, I have room for you.

