Yeah, good point, it's been a long time since I dealt with a new area for a bounty. I must've overlooked that perspective.
But the level differences gets greater and greater the higher levels you get, so a level 28 leader with survivors not far behind might not take as much time to get consistent successful missions in the new area, than a level 55 player with survivors still in the low 40's. So it's a lot tougher now, and the problem of under-equipment is more pronounced and problematic than it is when we were low level.
Then again, at least it encourages us to challenge ourselves?
A good counter to this problem for players of any level is the "Trained" book. Having survivors in the low forties, they can't use m60s or m416s, two of the best mission weapons for high level areas. Using a trained book, your survivor who is stuck at the early forties can use these weapons. Trained books are also fairly common, and if you can't find them, they are cheap as dirt to pick up in trade. As far as not having decent m416s and m60s goes, you can also pick up decent ones cheap as dirt in trade. Many average 2/3 m60s/m416s are more than enough to complete missions in levels 50+. To buy a decent ar or lmg and enough trained books to last a week, it wouldn't run you much more than 5-6 keys, or roughly 790 fuel (including trade costs). Not exactly breaking the bank there.
Also, what fun would the game be without a little challenge?