Poly games can get really complex, the more you play. You have to lose a ton of games with different tribes, different maps, in order to improve. Some things that slows the progress are in my opinion: to queue many fast games and not really care about the end result, rage quitting and not spending time to analyse the replays and detect the subtle reasons for getting behind. The opponents will do some neat unexpected things that you can try to test in the next games and get more knowledge.
Very dependent on how breakable the chokepoint is. If you know you cannot go through it even using giants then you should just not go through it as that likely means your opponent cant go through it as well. So if there are no ways to go by land then you would put your full focus into going for navy. You can even try using the units that havent went through the chokepoint yet to keep up the pressure and make your opponent concentrate on keeping up their defense while you go for sailing. This usually happens on lakes maps so when you realise your opponent isnt on the same mass of land as you and to get to him you need to go through very tight land then you rush for sailing
I love the video, and going with the teaching of asking questions to improve, I want to ask: When do you resign a game? At what point do you confirm that you going to lose, if it even is possible to confirm?
There are a couple of ways people use to identify when to resign. First, if an opponent is double your score past the first few turns that would indicate that you are probably losing. If your opponent is better than you or the same skill as you and they are the agressor, constantly sieging your cities and you know they wont play worse than you then you resign. If your opponent is worse than you then you should never resign as chances are, your opponent might throw their advantage away.