I was thinking about getting into a bicycling related industry where they may encourage you to take trips like this. Is there anybody here that work for such industry or company that can provide some insight?
I don't, but my brother worked for Trek for years. Unfortunately, I would NOT assume that being in the bicycle industry would lead to long tours.
I'm in the same boat as you. I've been at my current job for four years and just broached the topic of unpaid leave with my current boss (I'm in government) as a way to free up money in his budget. I don't know if it will work. The other strategy I've considered is setting my career on a path where I would be in positions that are viewed as short-term, creating the opportunity for breaks of a few months in between. I MIGHT be able to make this work for me, but for most people it is probably too risky.
As paddleboy suggests, it is all about your life situation. As you alluded to though, if you are willing and able to cut your expenses (or if you are lucky enough to have accumulated the assets) the amount of risk you can tolerate goes up appreciably. There are many who choose to live with less.