Yea, I think the earliest possible time to win is the 1st of the 2-plane cards. And even then its only if the cards are perfectly ordered. You need a total of 2 or fewer condition cards, not just 2 cards with conditions listed on them.
So going out every round means taking several negative status cards every round, resulting in the potential for death faster than you can heal it.
Yep, at 3 planes it's impossible to win. At 2 planes, there is a slight chance of winning and at 1 plane, there is a guaranteed chance to win at some point. You have to grab that chance so by the end it's really worth going out often.
Early on, you would get a lot of bad condition cards so you have to weigh your chances. But of course if you have some nice protective gear it might be good for the loot.