No Judge would look poorly on a lawyer amending an initial pleading unless no care or due diligence was taken when filing the initial pleading. If you learn new facts in discovery that would require you to amend your complaint and you don't, you will lose credibility with the judge when the court has to waste judicial resources on a motion to dismiss or a motion for summary judgment.
Texas has very lenient rules for amending pleadings. Under Rule 63 you can amend pleadings without leave from the court up until the week before trial as long as the amendments don't surprise the opposing party.
In Texas the hearing on September 3rd is considered a 'trial' for the purposes of Rule 63. So, Ty breached the Rule 11 agreement by filing late and then breached TRCP Rule 63 by filing an Amended Petition less than one week before a 'trial.' We'll have to wait to see what the Judge makes of that.