Welcome Andrew - here are some general answers to get you started:
Bees will swarm as many times as they can when they’re healthy during an abundant nectar flow. We do our best to manage this natural reproductive behavior but even experienced beeks can miss the window. The reality is that sooner or later, you will need extra equipment. Flow kits are pricey but regular Langstroth gear is widely available and much more affordable, so look for suppliers near you or use mail order folks. There might be beeks out there who never expand their apiary but at some point they have to offload extra bees to someone else to do this. My apiary floats somewhere between four and six hives, with temporary expansions due to splits that I sell and/or eventually recombine. If you get a package this year, it’s very unlikely to build up enough to swarm this season however. A nucleus colony or nuc is another story - a nuc is 5 frames of everything in a functional colony, that is ready to expand and will do that like lightning in a good nectar flow. A nuc started in a good season can definitely build to swarming level in a few weeks.
Regarding the super - like your swarming questions, much depends on the context at hand so there is no one-size answer about how much honey you can take. Back to how you start the colony, if it’s with a package, in NC and most of the US, you will be lucky if the bees fill the brood box to the point of being ready for the super within a typical nectar flow period. When we’re talking about a Flow super, the bees then have to wax up the cells to seal and extend them to be ready for nectar deposits. Wax requires abundant nectar, and bees switch gears to get ready for winter at the first sign of a waning flow. Some people run single deeps that they successfully overwinter by insulating the hive and feeding the bees in cold months. I would never advise leaving the Flow super on in any region where nights can get below 50F - not just because of the chance of crystallization, but more importantly because -
a) leaving the queen excluder on risks her death when the rest of the cluster moves up to get to the honey, but
b) taking it off risks allowing her to lay in the Flow frames which is a big cleanup headache.
So, Fsupers need to come off in late summer or early fall, with any remaining honey harvested out before storage in a cool dry place and sealed off from pests. The amount of honey needed in a hive to overwinter a colony depends on many factors, like the population size, the length of time before there is forage again, and how cold it gets.
My best advice to you is to take a class, keep reading here, and watch videos by experienced beeks who want to share their knowledge, not sensationalize. Our very own @JeffH is one of the finest examples and has loads of wonderful videos as well as posts on this forum to learn from. @Dawn_SD is another gold mine whose posts always enlighten and encourage. And there are many more helpful, friendly members here whose input will be invaluable!
Let us know when you get your bees and how it’s going! 
