Most of them, depending on your perspective. The one generally considered overly cautious is General McClellan, who led the entire Union Army in late 1861 and early 1862. Even with extreme superior numbers in men, cannon, and supplies he did not attack South for months. When he finally did, he moved south around Richmond and landed on the James peninsula, then slowed his assault as he believed his force was outnumbered 2 to 1. He was eventually relieved of command after the debacle of the Seven Days Campaign and his terrible inactivity.
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They might have done so, but both sides had seen the problems associated with green troops. The South may have been overly cautious, but they also had suffered in this battle.
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That could mean Ambrose Burnside or Ambrose P. Hill.
The courthouse was close by, still standing and not damaged by the war, so it could accomodate the combatants. Confederate General Lee surrendered to Union General Grant.
Yes. He was scared to lose his troops and allowed advantages that could have helped the Union to slip by.