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The only problem with the timelines though is that the port doesn't appear in the first days; I did a custom scenario, and it didn't appear until about a week in. Plus, it takes about a week to execute the escape: 2-3 days for him to see if you're interested, and another 3-4 for him to come back saying the plans are ready. At best, you can probably escape in 2 weeks. I think I escaped on day 16.
Karel, the guy at the port is legitimate. I wonder if it's possible for him to scam you or something, but accepting his offer is how you get the 31st achivement.
When you visit Karel at the port, he'll tell you to stay away from the Airport because it's 'too dangerous' or something, so it would make sense that he's trying to keep you away from that guy at the airport (and vice-versa). Maybe they just don't like each other. I saw in one thread that someone said Karel didn't show up to take them away, so it could be possible for him to scam you, but so far, the evidence says no.
Karel, at the Port, will say that you should stay away from the Airport (he says it's dangerous, but not really - there are only 2 soldiers there). The guy at the airport will tell you not to trust Karel (apparently - I killed the guy right away and didn't personally see his dialogue).
In other words, it appears Karel and the Airport guy may have some kind of grudge against each other. Or maybe Karel knows the guy mistrusts him, and tells you to avoid the airport because he doesn't want that guy saying bad things about him.
If you're worried about the achivement, just do a custom scenario. I made a game with no winter and low crime, then just breezed through to escape the port.
For new players, I'd recommend just waiting for it to come up, but for veteran players wanting the achivement, better just to do that. Took me about 16 days to escape by the port.