I think Jeb gets a bad rap in history, first he was given orders by Lee to scout the Army of the Potomac to see if it was following him. I'm not quiet sure about how many miles he traveled in doing this mission but it looks like he traveled quiet a bit in doing this mission. It looks like maybe this mission lasted about a week and covered about 70 miles or so. To expect Jeb to stay far behind you as you march off far ahead of him into Pennsylvania wasn't to smart. Both Lee and Staurt were working in enemy territory, so Lee should of known that the odds of Staurt running into unexpected trouble would be great, which he did. Considering the mission that Lee had in mind he should of not sent so many Cavalry men off with Staurt and should of kept half of them in closer vicinity of his troops positions. If Stuart had a smaller mission like say a two day mission before he met with Lee again it probably would of turn out different, considering Staurt ran into probably many more skirmishes then he had expected which slowed him down. I think at this point Lee was taking too big of a gamble, and the cards in his hands were not that great.
Charles Marshall gave a speech in January 1896 to “correct the impression that has prevailed to some extent that the movement of the cavalry was made by General Lee's orders, and that at a critical moment of the campaign he (Lee) crossed the Potomac river and moved into Pennsylvania, sending the entire cavalry force of his army upon a useless raid."
The fact is, Stuart was ordered to the east of the Bull Run Mountains, to get between the Union army and Washington, to gather supplies, damage communications, and march to the right of Ewell... Early being at York.
Stuart's communications were to be with Ewell. It would be nigh impossible for Stuart to communicate with Lee about the movements of the Union army. For that job, Robertson and Jones were left with specific orders to move to the right and rear of the army as it advanced into Pennsylvania.
Stuart received three orders (if you count the one reported by McClellan in his biography of Stuart. Since details of this order show up in the official report, it probably did exist) telling him to march east of the Bull Run Mountains.
Stuart's orders on 6/22 were clear. Lee wrote: "If you find that he (Hooker) is moving northward and that two brigades can guard the Blue Ridge and take care of your rear, you can move with the other three into Maryland, and take position on General Ewell’s right, place yourself in communication with him, guard his flanks, keep him informed of the enemy’s movement, and collect all the supplies you can for the use of the army."
Longstreet endorsed the orders: "I think that your passage of the Potomac by our rear at the present moment, will in a measure, disclose our plans. You have better not leave us, therefore, unless you can take the proposed route in rear of the enemy.”
Where as the 6/23 orders a more confusing, they still order Stuart around the Union army. The only contigency in which he was to cancel the order was if he found the Union army marching any direction but north.
The only discretion left Stuart was whether he could get through the Bull Run Mountains. He could and he did.
Lee was not without cavalry. He had plently of cavalry with him. On 6/30, Lee knew that Buford was in Gettysburg and generally where the Union army was. Harry Heth brought on the battle by going for shoes with his entire division and artillery. Which would be true if Hill hadn't already notified Ewell on 6/30 that he was going to Gettysburg to find out exactly what was in front of him.
But no matter... On July 1, after the day's battle, Lee made the decision to attack. It no more had to do with Stuart or information.