So I just finished my first campaign game, and the "victory" felt so empty. I was actually surprised by it, and considering it was in a small little popup box, it didn't feel like much of an accomplishment. I've never felt so let-down winning a game before.
I played as the Union, and for the first 3 years I got my ass kicked all over the continent. From west to east:
Far West: I lost every battle in Arizona and New Mexico. And then in late 1862, the Rebs either moved their guys east or everyone died, and my California column moved one space east per turn until finishing the war in Laredo.
Rockies: I had Blenker out there with a half-strength division. He got his ass kicked from Oklahoma to Colorado for a year. The second year, there was noone left to fight, so he spent 1863 retaking all the forts he got kicked out of in 1862.
Trans-Mississippi: I 'hid' the crap generals Butler and Halleck out here. I basically conceded Missouri to Polk, and Watie spent a lot of time beating up milita units in Iowa.
West: Grant and Sherman marched right down the Mississippi, before being "captured" by Memphis. If they marched out of the city, they'd either miss the battle or lose a battle, and while marching out they'd lose Memphis. If they stayed in Memphis, Forrest could take his army and gallivant all over West Tennessee, Kentucky, and Arkansas. I spent 1862-3 losing battles and/or hiding
In East Kentucky, I raised a huge army under Buell to move on Nashville. Well, that never happened. I ended up using that army to chase down whatever threat came north- Polk from Missouri to Illinois, Beauregard into Ohio, Forrest into Indiana. I didn't capture middle Kentucky until November 63.
Shenandoah: I raised an army in Pittsburgh, intending to move it down the valley and come out behind Richmond. That plan failed immediately. I got my ass kicked all over West Virginia, and spent 1863 chasing a huge Stonewall Jackson army from West Virginia all the way to Chicago.
East: I did not fight a single battle until 1864. I took "maneuvers of opportunity" and ended up encircling Richmond, but the first battle the army of the Potomac fought was when I conquered Richmond in 1864.
By sea: Landed division in Norfolk. Got wiped out. Landed division south of New Orleans. Got my ass kicked and barely survived in the forts.
Then suddenly the south ran out of troops, and I marched south taking whatever I wanted during the spring of 1864 and won.
tl;dr
Got my ass kicked for 3 years. Fought every battle on my territory. Then the south ran out of troops and I won. Still felt like I lost.