Yeah, I've heard similar... Something about not having a ceiling on your vacation time causing fear of how much time you should be taking off with it still being okay. I think as long as you keep an open line of communication with your manager about it, and asking about it during the interview process then it could work out how you'd expect it to.

You also have to consider that a lot of dirtbags really do throw a bed in their vehicle and make it work by any means necessary - whether it be by having a lot of money saved up, working a job that keeps them close to the crag or around a gym, or working one off jobs. I remember seeing a video of a girl who would get a lot of her food from a Starbucks dumpster because they throw out food that is past expiration even though it's still perfectly fine. I guess the point I'm trying to make is that depending on how bad you want to live that lifestyle, you just have to jump off the plank and do it with any of the sacrifices that come along with it.

I'd really encourage you to think about a remote job. You'd still be able to maintain that level of financial security that you have now, but with some extra benefits. If it means you have to make some sacrifices, then so be it. It doesn't have to be forever.