RE: fletching
Feather fletchings, although there are ways to get by with plastic (certain types of rests).
Glove or tab is your choice. If you go with a glove, try them on to get a proper fit--you want it really tight when new, so it's not loose when it breaks in. I shot a glove for years, but am trying to switch over to a tab because I get a much better release.
How long it takes depends on the individual. Start now, with good instruction you should be ready to hunt by the time season opens, although you might want to restrict yourself to closer shots.
Chad