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If Lee had won on the 2nd day of gettysburg he would have had the man power to maybe take baltimore. If he had taken baltimore where the majority of it's citizens was pro south Lee could have made up for the losses he suffered at gettysburg.
Lee marched into Maryland in '62 with all flags flying and bands playing "Maryland my Maryland" with the intention of filling his ranks with pro rebel Marylanders and the response was underwhelming, why would it be different this time? Admittedly it would be on the back of a victory but if those pro southerners had not joined up to fight pre '63 I think it unlikely that they would do so now, volunteers were getting hard to find and conscription was the way of filling the ranks at this point in the war.
The problem with the invasions of the North (there were at least three, counting 1862, 1863, and Jubal Early in Chambersburg in 1864) is that the Southerners took the easiest and most natural route from Virginia, up through the valleys that extended north of the Shenandoah into western Maryland and south-central Pennsylvania. This was not a useful or sympathetic region, and it stretched the supply line so badly that Lee never made it to Harrisburg or Altoona, his intended targets. A better strategy would have been to invade pro-Southern tidewater Maryland and Baltimore, but the risks and costs must have struck Lee as overwhelming.