Time for clutch work, need help?

I'm curious what you exactly mean by hard engaging?
If it is just high rpms before engagement, you may just want to change out weights and or spring. It sounds like that may be the case if it has done this since the kit was installed.
Engagement is in heel weight and primary spring initial rate. A number of the aftermarket kits go with higher engagement to achieve holeshot. Some of the kits are hard to trail ride in slow stuff. It's all or nothing right off the line.
Hopefully it's that simple. I don't recall the exact parts in that kit for the Cat primary. Do you know the spring rate? Did it come with adjustable weights?
The reason that I mention the term "hopefully" is related to clutch life. How many miles are on the clutch? When they start to wear out, engagement can also be affected. Generally you would also see odd rpms in the shift as well. Those could really get out of whack on top. Those clutches liked to show wear in the rollers when they start to go. That is easy to check by using a finger to "roll" the roller. If it isn't smooth rolling, it may be time.

Sorry, I can't help much with another brand primary. I have to ask though. You went with the Team secondary? Do you mean the Boss version along with jackshaft swap? I'm asking because that would allow you to put in an ADAPT if your primary is ****ed.

Uff, that is pretty high engagement for normal trail riding.

Hard to know for sure if the number stamp is the spring rate. (Can't remember if Speedw puts the rate on their springs.) That rate would be higher than stock. Sounds like you may have the weights with adjustable heel? I'm not going to give much input on tuning because of the following.

Unfortunately, the roller isn't good news for long term. You might get by for awhile, but it will keep getting worse. How was the weight on that roller? They usually start showing wear spots when rollers hang. That will also get worse. Eventually, it can even "lock" the shift if they get real bad.
That's already a fair number of miles and age. You can try limping it longer, but if the weights are already wearing they go downhill pretty fast. I've had a few that were rode past their expiration time and they were super sloppy on take off and holding speeds. It's possible that you experiencing the wear symptoms along with the higher engagement of the kit.