Darn it you're right. I re-extracted your saves and the supposedly first on I'd used is now similar to your 6th as the wedding with Jasmin is about to start. One of my old files most have lingered around in the game cache even though I did put all of them in a backup folder before hand ...
I tried a couple of things with the Jasmin marriage folder, but no matter what I do in the week till the competition it only ever gets to second place for lack of flexing ...
So now I took a safe that's definitely yours. Skipped ahead a year. Tried the hole thing again where I did nothing but Strength Stuff for all of January ... and I came in second place.
I have no idea what's going on anymore ...
Edit: I tried again, for maybe the hole skipping part de-trained the old man to much. This time I took care to sleep once and train twice a week (usually I only do once, but just in case) for the hole year up until Spring, when I started doing nothing but sleeping, training, massages, tea, even a harvest - basically everything that's strength/energy related for the hole season till the day of the competition. And it nonetheless only got to second place...
2nd Edit: I wanted to give this a final try. Played through the hole year from your first save with no skipping. Did nothing but farming, training, sleeping, massages and tea. With this exact method I was able to win the contest on a fresh file in year one. Nonetheless, it was only good enough for 2nd place. I fear your file is simply bugged ...