Teams not having handicap when Sum of Bowlers Handicap is selected

Check your rules under Setup > Rules > Legal Lineup, ‘When advancing to  the next week, adjust the team roster members by:  leave bowlers as they were.

Once that has been changed, go to Weekly, Adjust Team Rosters, put your rosters in the order they wish to bowl.  Click on Save as Default Roster Order.  If you change the roster order either by removing a player and or replacing a player, re-click this button.