Speaking Softball Canada (because that's what bobbrix officiates, iirc). . .
1) As others have already said, it's a two-base award. See Rule 8-7i:
Quote:
Runners are entitled to advance without liability to be put out when a fair ball bounces over, or rolls under or through a fence or any designated boundary of the playing field. . .
EFFECT - The ball is dead and all runners are awarded two bases from the time of pitch.
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2) The Softball Canada ruleset is not explicitly clear about what constitutes a legal catch in this case, but it is covered in the case book. See cases 1-36 and 8-88.
For this to be a legally caught fly ball, the fielder must first touch the ball while any part of his/her body is still in playable territory and must establish possession before any part of the DBT is contacted.
When there is no fence, then theoretically the fielder can leap for the ball and make a legal catch provided that s/he touched the ball before his/her trailing ankle crossed over the dead-ball line and that s/he didn't bobble the ball after coming down in DBT. Of course any runner(s) would be awarded one base.