>>1995783We were all retards once, my retard.
>where to start? Start with day trip, then one-nighters, weekenders, 1 week and so on. See if you even like it. Any bike can do initially. Use a backpack for a day trip. Borrow panniers/gear. Buy used. If you've got money start small to see if you enjoy it.
>Do you guys sleep outside? Yes, in a tent. Stealth camping is a thing, but ask permission if you can / be bothered.
>Do you book hotels on the way? I do at least. For long 1+ week tours, a hotel is a great way to relax, visit an area, do laundry etc... I never book ahead, usually on the day, or at the place.
>How long do these trips take? (I have a job so taking days off is suffering) Anywhere between a day, a week, months, maybe up to a year. Best time to do it is between jobs, and if you have a place to store your stuff and a means of covering your rent.
>Any gear you'd recommend for a total newbie?Try it at first, you probably have everything you need. Bike, backpack, a pump, some puncture kit and don't forget sun-screen.
When you get really into it, you can question if your bike is up to scratch and start researching bikes, panniers, navigation and so on. It's an iterative process. One thing I love is people converting old MTBs into touring rigs. But that's later.