How do I invoke a D.S. al Fine type of action without it skipping immediately to the 2nd repeat. Is there another options available? category:8

Yes, Both checkboxes for the Play Repeats and Play Repeats after D.S./D.C. jump are checked from the location you indicated.
What I was hoping to achieve is jumping back from the end of bar 146 back to bar 9 and then play both first and second endings again of the melody section and then invoke a To Coda at the end of Bar 42 near the end of the melody section and jump to the Coda symbol at bar 146 which plays to the end of the song on bar 158. The only problem is the Segno just skips to the second ending. since I have yet to find a workaround did away with the rest in the melody section which resolved the issue.