Hey mate, I loved the Wastes and appreciate the core gameplay loop more than Warsims personally too.
Unfortunately at the time I never expanded the skill trees, so only the skills with numbers next to them work in game.
As for the regions, yes they are all completely random but at game start the initial loadout are all lower level regions that are super small. This is to ensure the player doesn't instantly get killed off with a bad loadout. After that it's pure luck. There are perks that make it so you get a guarenteed higher minimum of regions to choose from but they are still random.
It's a mix of tougher spawns but also some encounters that are hidden for lower region levels, lockpicking is unchanged though.