Does it make sense that a Lower Rated team plays your team, and because of the handicapping they beat you barely. But then in the overall standings it doesn't matter at all, your team still got their points so you remain in 1st place.
Let's say you have 8 teams, in week 1, the top handicaps all play the lower 4 handicaps. Team 5 beats Team 1 with the handicap by 1 pt. Team 6 beats Team 2 with the handicap by 2 pts. Team 7 beats Team 3 and Team 8 beats Team 4.
In your standings all 4 of the top teams Lost their matches, but you will still rank them the top 4 teams and all the teams that won would still rate 5th-8th place.
1st Place, Team 1, Most Points, 0-1 record
2nd Place, Team 2, 2nd in Pts, 0-1 record
3rd Place, Team 3, 3rd in Pts, 0-1 record
4th Place, Team 4, 4th in Pts, 0-1 record
5th Place, Team 5, 5th in Pts, 1-0 record
6th Place, Team 6, 6th in Pts, 1-0 record
7th Place, Team 7, 7th in Pts, 1-0 record
8th Place, Team 8, 8th in Pts, 1-0 record
(I know this is a very extreme case, but it mathematically could happen this way.)
Imagine winning your first match and seeing that you are still in last place.
Actually this could never happen since handicaps are established by by averaging a players scores throughout the season. Your example shows basically 1 week in play.
Also, I think you may be understanding the system wrong, there is only 1 trip prize for the regular season. That is awarded to the team with the most points (not including handicap points). This would be the team that played best all year.(Why not reward the best)
After that is all said and done. Ranking of ALL of the other teams is done by round points. The top 3 teams (round points) at the end of the regular season are awarded a small cash prize.
AFTER that, there is a playoff with the teams being seated according to their ranking (by round points). This play off is for the remaining trips and cash.
This is a very fair system in my mind. It rewards the team that plays the best all year with a trip while giving everybody else a chance to win a trip in the playoffs. Those that don't win a trip win cash all the way down to the last place teams. (of course they don't win a lot)