NOOB Bikepacking Questions

Hi All - I have a couple of total noob questions. I have been biking longer and longer distances to get in shape, but haven't gone multi-day yet. I love the idea of self-supported long distance bike touring, and the freedom that comes with it. Not really jazzed about hotel to hotel riding although I'm sure a hotel is quite nice once in a while. In riding long distances...


1. Where do you camp? Can you just find a place to crash usually within a few miles of where you end up? Or is some level of nightly destination planning necessary? The Trans Am Bike Race /Inspired to Ride style seems really attractive - but the sleeping situation seems a bit sketch. How do you overcome this?


2. How much bike maintenance should I know to have confidence that I can get out of most situations in the boonies (e.g. a broken spoke?) I know how to grease my chain and fix a flat, can figure out a few more things I guess but don't feel very confident to go too remote in case something breaks.


Thanks!