Just wanted to add a quick update to this old topic to let everyone know that Version 4.0 included quite a few new bridging options.
1) A new bridging algorithm was added which typically chooses a much better initial direction for the bridging fill. I tested it with the model you posted above, and the default direction is much better.
2) If you want to customize the direction of the bridging, you can also do this by going to the Other tab of your process settings and enabling the "use fixed bridging angle" option.
3) There is also a new option that will let you customize the exact settings that are used for the perimeters of the bridging regions. This can also be enabled on the bridging tab by checking the "apply bridging settings to perimeters" options.
In case it helps, there are more pictures of these changes at the bottom of the page below:
https://www.simplify3d.com/software/rel ... ion-4-0-0/
Thanks for the great suggestions!