There is some trade off in flat v cylindrical. I've had flat starts with a city in one corner and another city in the other corner by turn 20. That's expensive.
I run into this scenario quite a lot on a Great Plains map, where the HOF rules force us to play with a Flat World Wrap setting, but an AI has their capital in the opposite corner of the map, which I then capture.
I'm assuming, though, that you're talking more about getting Settlers from Huts and deciding that you like the area where the Settler appeared, which can be literally anywhere on the map that a Hut exists, including at the opposite side of the map.
Given a map type with a lot of land that could be connected via a Cylindrical or Torriodal World Wrap setting, it's hard to know whether the extra convenience will be worth the extra Maintenance cost. I suppose that it's very situational, with the ability to pop Settlers possibly leaning toward wanting more wrapping, not only to reduce Maintenance of distant Cities that get settled early on but also to allow for easier access to some of the Huts.
But, it is also easy to forget about the world-wrapping and have an AI sneak up on you--even on Settler Difficulty, an AI can take your City if you don't see his/her Warrior in time to defend your City that you likely left without a defender.
It's not uncommon for me to have 8 - 10 cities by turn 40 even on a tiny map. Once I had 12 ...
That's quite a lot of Cities! About what percentage of those tend to be captured Cities versus Settlers-from-Huts Cities versus selt-built-Settler Cities?
Circumnavigation
Another noteworthy point about the World Wrap setting is that on a map that has some or a lot of water near the edges, a Cylindrical World Wrap setting (or even a Torroidal one) will enable one player to earn the Circumnavigation bonus. On a Flat World Wrap map, you can't Circumnavigate, which just logically makes sense, since the concept is that you're playing in only a limited region of the world and thus aren't travelling all of the way around it.
So, on a Terra map, where you're likely to be the one to Circumnavigate, you do need to decide whether that +1 movement point is worth getting.
On some other map types, such as Big & Small, where it's very easy to Circumnavigate in some cases, you can often get beaten to the Circumnavigation bonus by an AI, meaning that having Circumnavigation available can actually be a relative penalty to you, since then one of your competitors will have fast-moving Galleys and Triremes. I've had several of my Galleys sniped in this way, since it's harder to see enemy ships that are 3 squares away, perhaps hiding inside of a nearby AI City.
