There are a variety of subtle "tricks" when it comes to preferences for winding strings at the post. The way I learned to do it (which I wouldn't necessarily recommend to anyone) is very simple and basic, but slightly risky for having a string snap off at the post. In 40 years of playing, however, I've only had one or two strings break there (and as I recall, they were both a very light guage high E strings). At any rate, if one wanted to learn about various ways of doing it, I know there are quite a few tutorials on the web, particularly on Youtube.
In terms of preferences for frequency of string changes, I think that's highly subjective. The "brightness" of new strings is not a positive thing for a lot of players, including yours truly. It's less of an issue for me anyway, since I prefer flatwounds, but I still don't like the brighter sound of brand new strings. Personally, I don't change strings until I encounter intonation problems. I've found that I can typically keep the same strings on for at least a year or longer*, as long as I wipe them down after every playing session (which I learned to do habitually many years ago). I also gently wipe the fretboard and the back of the neck (with a different cloth) after every session.
(* When I play, I don't do a lot of serious string bending, which I'm sure contributes to the life of my strings)
I should also add that since I own six guitars, which all get played pretty regularly, the strings on each one get much less use than if I only owned one guitar. In other words, "ymmv".