If you lose often to teams which seem to be weaker you should think about your tactics and special attributes of players. Another problem of CF Montreal is age of players: old players have usually lower endurance and get tired faster. Star value is not everything. I remember years ago team from Estonian league with highest average star value, but finishing only in mid-table as he had not enough attributes trained (his non-correct defenders and DMs picked loads of cards and penalties/freekicks) and squad was aging, when refreshing it he was relegated and stayed to lower leagues for 2 RL years before coming back to top.
You have had your team just 2 years and it hasn't yet top facilities. You need at least 2 more levels of stadium for bigger income that let you manage FA (and YA). With FA3 and buying in couple of good youngsters every season you can compete with two top teams. My second teams has been 5 years and now is aiming for their first league medal. In different leagues there are many teams who started quite early years, but now are starting to earn first bigger success, so patience in the key word.
And...why do you pull so old youngsters-18? They will be finally always far behind those who are pulled with youngest possible age. At 21 there is clear difference of their level and price. There is also no point to keep in squad 30+-aged benchwarmers who barely get some matches, their value only decline faster than on first team players. Buying old players to first team is probably easiest way to some quicker success, but it will not last long and is not financially efficient.