Totally and surely have that same feeling, and that is also exactly why I have joined the current platinum association and stayed there despite being a constant fight against relegation for all 4 seasons in a row (asso always finish within 1350 and 1400 points, and none are tankers , so it is easy to imagine what the pressure of getting 250 points every season could be like).

Even worse is that 50%+ of the time my asso match-up would be at least 5%-8% better (another 25% about 3%-5% better, and only 4 opponents were worse [can really count as they were so rare]), so it really forces me to set up and master on how to win via counter against opponents of up to 10% better, and also properly build my team to win by those 7-0 or higher margins in all other daily matches with a 20%+ advantage. Semis and finals opponents are tough too, as it is very normal to be drawn with similarly draw manipulating managers too.

This is probably the most balanced approach that I personally would take when I would like to:
1) Win all trophies - to show (off ) competitiveness
2) Maintain platinum with the current fight-for-survival association - for the Ts reward, and also a very good weekly training ground against better opponents
3) Aim for a minimum 7-0 wins or higher for every daily matches with 20%+ advantage by testing all different formations, tactics and in-game substitutions possible (the ‘default’ margin is about 4 to. 5-nil, and getting 10-0 wins is a sign of doing the right thing)
4) Achieve some great 300-game unbeaten run or 100+ winning run would be fantastic
5) Keep manipulating draws to save resources until it doesn’t work (when it gets to higher level, this won’t work anyway)

As you say, each of us value trophies, achieving records, company within associations, and very probably winning an unlikely trophy by beating opponents as an underdog differently. Each of those has its own sense of achievement and enjoyment within too.