PosGIS: Longest line connecting point to line

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I have a point and around it lines and polygons in the rule of obstacles.

  1. I want to connect the point to each of the lines, with a line, such that this connecting line is not intersect any obstacle (polygon) on it's way. Note - sometimes it's my be not possible - means there will be some lines that the point won't be connected to them (because any connecting line will intersect obstacle).
  2. When it's possible, I want to make the longest connection.
  3. For the completeness of the question - What about same variant but with shortest line?
  4. And let's take one step further: What about same rules but connecting 2 lines? (Instead of point to line).
Thanks,



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