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At what point does it become a material change in circumstances that justifies a modification to custody orders when you've got your child a much higher percentage of time than ordered by the court?

I've got 50/50 custody by order.  The last year and a half approximately, my uBipolar/BPDxw has been taking horiculture classes and working for a tree service company.  The classes have cut into her time, and I've had S9 at least 1 of her nights each week, and sometimes even 2 as she's got night classes.  I've also ended up with S9 on short notice during a lot of other instances when she'd get a call for some tree service job related thing and have to go to a job site where she couldn't take S9.  This includes weekends.

I'm more than happy to get S9 during these times.  And after uBipolar/BPDxw's past of really refusing to try to make something of herself, I think there's a good part of this in that she's actually exercising some good work ethic and ambition right now.  In short, she's not being a waif currently.  I do believe she in some kind of idealization phase with the tree service owner.  S9 tells me the owner sleeps over at his mom's house a lot now, which doesn't bug me.  The guy owns his own business and operates it successfully, and I've heard nothing to suggest his at all dangerous in anyway.  The one time I met him I didn't have any redflags go off.

However, I added it up and depending on uBipolar/BPDxw's class schedule, which changes each semester, and I've had S9 a minimum of 60-65% of the time just from taking him extra during his mom's night classes each week.  I haven't added in the other random times when she's had to go do tree service work that I've taken him.  I'm currently paying CS to the tune of $600+ per month, and it's definitely not being used to support S9 as he's with me most of the time!

I'm also concerned about the chaotic schedule now.  We're supposed to be one week on, one week off, but at the moment it's I've got my week, and then I've got him half her time on a continually shifting basis.  The lack of routine for S9 during his mom's time concerns me.

So does anyone have any thoughts or experience in how long it has to go on before a court would say "yeah, a new precedent has been established, changing the orders to give Waddams majority time at this point is in S9's best interest" ?

Joint custody, right?  Is it official Shared Parenting?  If so then you may need to file for Change of Circumstances.  To get the informed local response it sounds like a lawyer/legal question, so time to give the L a ring.

Who is residential parent for school purposes?  If you're seeking to have majority time then of course you need to be sure you become residential parent as well if you're not RP already.  And make sure you've saved all communications about the extra time since she may very well deny it.  What made a difference in my case was that I had several incidents of ex's poor behaviors.

If you're not in Shared Parenting or some other form of 'official jointness', you can possibly file with the court a motion for Modification of Parenting Time, Residential Parent and Child Support.  Sometimes lawyers put in a lot of documentation, sometimes just the outline, your lawyer should know what to include.

How will she react to the court motion?  Is she a possessive entitled mother or one somewhat distances and more interested in adult relationships?  How entitled is she of her child support or being seen as The Mother or Mother Of The Year?  Those are the huge factors.  Likely, if she's anything like my ex, once you file she will stop giving you extra time, might stop her classes or leave your child with her boyfriend or others while she is away.  However, now is a good time to take action since she is giving you extra time NOW, she may not give you as many additional overnights once her classes are completed.

My lawyer told me Modification of Parenting Time case would be much simpler than my 1.5 year Change of Circumstances case where I was seeking and received custody.  Ha!  It's 1.2 years and still counting.

Not knowing your precise legal standings as parents and what it would take to modify the parenting time schedule, the best answer might be obtained from your lawyer.