Add an NHL season simulation for NHL teams,Expansion teams and Fantasy teams.

Can you expand on that? Not sure I fully understand your request.

I imagine its something along the lines of what NHL18 does where you can sim all the games in your season as if you are a GM and you get to see how many points each player has and what not.

I wouldn't think this is feasible, is it?

Feasible, but not a small or even big addition to the site. Resources and man hours required would be much higher than any sort of payoff.
Not some sort of addition to CapFriendly, but a completely new project, possibly partnered up with CF to interact with their systems/userbase.

So for all intensive purposes, unfeasible.

Would be a really cool idea but I can see how that would not be on CF's radar of things to do for a long while.

It could be good for the GM Game but it doesn't seem like it would be easy to do.