How difficult is Love for Sail? Can you die or get into unwinnable situations?

You cannot die or get into unwinnable situations in Love for Sail. It's one of the later Sierra titles, after all.

It is pretty difficult though. Not insanely, but it's very challenging.

Thanks guys! I'm gonna buy it. Don't mind the difficulty as long as I can't screw up irreparably .

You cannot irreversibly screw up your game in the sixth game either. Although it's possible to die, the game gives you a "Try again" button that rewinds just before you killed Larry so no need to save every two minutes. The deaths in the sixth game are more of an excuse to throw in some extra jokes and/or slapstick than add any kind of challenge. So if you like Love For Sail and want another stand alone, player friendly Larry game, that one too might be right up your alley.