It's sometimes hard if you're not used to it, specially on gums inflamation and sometimes blood. that can also happen if you stop for a while and start flossing again; be gentle in that case, enough to massagem and increase intensity with time.
It makes my gums bleed because I haven’t been flossing regularly for a while until now. I’m sure that after it becomes a habit, you won’t have issues! If you’re having trouble with the actual process, look up some videos.
Sometimes. Most of the time I'm just too lazy to do the extra two minutes, but as soon as I start establishing a routine, it gets easier. Of course after a few days or weeks I just give up again, because my brain doesn't want the now old activity anymore.