For me the toughest part of initial swamp entry is the scouting aka searching for turnips. Of course I'm on the look out for crypts as well, and try to bag a few leeches and Draugr for drops along the way. I prefer to scout along a border between Black Forest or Meadows and Swamp, hopefully mostly higher ground. It seems the defenses to bomes ends up concentrated on the borders - not sure if that is actually true but seems like it.

Once I make the move into the interior of a Swamp things get much easier.

PS: biggest problem by far I have with the swamp is the darkness - my eyes aren't so good anymore and too much swamp gives me a headache.