It would be wildly out of character for him to have done that. Unbelievably out of character. In the realm of never having happened before. I don't know why that would be the first thing to come to mind.
I don't either. Stuart's raids in the past were conducted as "pick a smallish detachment of good men..." kind of thing. I don't know the details of the planning, but I do know enough on the actual raids that they speak of Stuart's careful planning rather than his "I'm a Jolly Cavalier Fear-less and Care-free" imagery.
But it comes to mind anyway. It doesn't help in this (Gettysburg) context that Morgan would demonstrate exactly what those kind (the irresponsible kind) are like, which produces imagery floating around my head that has nothing to do with Stuart but influences my easily biased brain anyway. Stuart would no doubt be (justly) offended at the comparison, but that's not the point.
Personally, by 6/30 or 7/1, I would be wondering if Stuart was dead and his command destroyed, particularly coming so close on the heels of Jackson's death. That is what would be on my mind.
Its certainly one of the more plausible answers to "why haven't we heard from him?".
Anyone who thinks Stuart disobeyed orders has clearly never read the orders, because he fulfilled them to the letter. I've always wondered what these people think Stuart was doing all that time. I hear vague things like "glory jaunt" etc, but no one ever wants to get specific.
As for Lee... if you want someone to be with you, don't issue orders sending them away.
He did take more time than he "should" have, if one pretends that his orders weren't ridiculously optimistic about the timetable. Even without the delays, Stuart should have realistically arrived closer to the 1st of July than earlier, in my opinion.
On being a "glory jaunt" or the like, here's what
Gettysburg: The Confederate High Tide (by Time Life Books) says that kind of implies that it was (as they call it: "Jeb Stuart's Untimely Ride"):
"Stuart's 4,800 men could not shoot their way through Hancock's large force. He could prudently ride back westward and maintain contact with Robet E. Lee's northbound army, or he could ride around Hancock. Characteristically, Stuart decided to follow the more daring course, taking his three brigades on a detour south and east before turning north. In doing so, he put two mountain ranges and the entire Federal army between himself and Lee's right flank."
The problem with that, which sounds truthful at first: "You will, however, be able to judge whether you can pass around their army without hindrance, doing them all the damage you can, and cross the river east of the mountains. In either case, after crossing the river, you must move on and feel the right of Ewell's troops, collecting information, provision, &c."
So the "characteristically, Stuart decided to follow the more daring course" creates an implication Stuart is choosing to err on the side of (unreasonable) boldness - where as his orders quite specifically authorize him to make such a decision
as he sees fit. Meanwhile, he's
expected to have a considerable distance between his troopers and the main army - though it might be argued he's also expected to link up with Ewell, that's not inconsistent with being much seperated from the other two corps of the Army of Northern Virginia.