Leading - when does it become too much?

TLDR:

• OP looks at 'leading' his wife and family by scheduling date nights, vacations, arranging babysitters , finding ways to have alone time, scheduling new novel experiences, etc.
• OP trying to reconcile idea of 'leading' his wife vs. overdoing it by giving too much too often and giving being taken for granted. Where is the balance to avoid being a simp?
• OP was led to post by idea of 'don't be more invested than your SO' and 'don't ever give significantly more than your SO' -- this idea is difficult to reconcile with 'leading' as a man
• OP trying to find the balance as OP is concerned that overdoing the giving creates too much security and reassurance where it's expected, possibly taken for granted, and boredom can set in

I have been through 85-90% of the side bar material in married RP. I lurk quite a bit and read a lot of the posts. There are a couple of ideas or concepts that I am trying to reconcile. One being that men with wives and families are leaders. OYS, make it happen, take action, do your own thing, etc. I do my own thing, yes, but I also take the lead on scheduling date nights, arranging babysitters, planning vacations, home maintenance/improvement, etc. At times, I feel as if some of these actions are taken for granted. Not always, but sometimes I feel as if I've done them so much that they are almost taken for granted from time to time. You don't ever want to provide so much security and reassurance that boredom sets in. This is not manipulative. This is being intentional about facts of life.

With that said, the second concept I am trying to reconcile with this is when does it become too much? When do my actions of leading (i.e. scheduling dates, vacations, alone time, etc.) become simp behavior? How do you find the balance between being proactive about building and improving your relationship vs. going overboard by giving too much or too often and becoming a bit of a simp?