Alright, here's my take on what a victorious Confederacy would be like:
- Borders: West Virginia going Confederate is out of the question. If the Confederacy tries to take it, they will have an epic guerrilla war on their hands. Kentucky also seems unlikely. Sure, the state had some Confederate sympathizers, but so did southern Illinois - the land of Lincoln. The pro-Confederate government that the secessionists set up was essentially powerless. Most Kentuckians were pro-Union, as evidenced in a special congressional election in 1861, when pro-Union candidates won nine of Kentucky's ten electoral seats. The sole Confederate victory was in the southwestern part of the state, which was economically linked to Tennessee. Missouri is a more interesting case. The Union won the battle there pretty early, and they needed St. Louis and the northern half of the state for trade with the western US, but the Confederate sympathizers there were fighting a fairly effective guerrilla war. The Union may get the northern half of the state, including St. Louis and the entire Missouri River area, while the Confederacy may get the Ozarks. The Indian Territory will probably go with the Confederacy, as the Indians are probably not too keen on the Union for reasons that should be obvious.
- The Union, post-war: American industrial development will likely progress as it did in OTL, as it still has a massive industrial base and tons of natural resources. The United States government will also become more centralized, having learned the lesson of the Civil War. However, any imperial ambitions that the US may have in the late 19th and early 20th centuries will be nipped in the bud. The prevailing thought will be, if the Union couldn't keep the South from seceding, then how can they hold an empire? This means Alaska never becomes part of the US, although business interests may still bring us into Hawaii. Also, the Confederacy will likely block any Union involvement in the Caribbean, and may try to compete in Latin America. This will butterfly away the Spanish-American War, which will in turn butterfly away the Philippines becoming a US colony. Civil rights are likely to progress much faster, what without the South holding the issue up in Congress and with the bad example that the Confederacy is setting. The civil rights movement could gain traction as early as the 1920s. The lack of the conservative Southern voting bloc will also mean that women's rights and gay rights will have a much easier time.
- The Confederacy, post-war: The Confederates are likely to be in bad shape down the line. Its economy is built on agriculture, particularly of the cotton crop. This leaves it highly vulnerable to price fluctuations and pests, which will kill King Cotton just as it did in OTL. Thus, it will have to industrialize. Northern Alabama, northern Georgia, eastern Tennessee, and the western Carolinas will have some industrialization in the early 20th century, but the Confederacy simply won't have enough resources to keep pace with the Union. Slavery is not likely to be phased out for decades. The South just won a war to protect their "peculiar institution", and they won't just give it up out of the kindness of their hearts. It will take events in the early 20th century - namely, international sanctions, industrialization, and the boll weevil - to break the power of the landed aristocracy and weaken slavery as an institution before it is finally abolished. Even then, civil rights will be a long time coming, and women's rights and especially gay rights will also be a ways off. Attempts to spread into the Caribbean and gain a Mexican route to the Pacific are not likely to end well, since the Confederacy doesn't have the military or industrial capacity of OTL's US. In fact, Mexico, looking to regain some lost territory and viewing the Confederacy as weak, may try to pick off western and southern Texas. And the Union will be happy to weaken the Confederacy any way they can. By 2000, the Confederacy will be much like Argentina or Slovakia - not a Third World country by any measure, but definitely not a developed nation, either.