As to whether VA tried to re-unify with WV after the War, yes: I posted an answer to that here. They asked, and WV said no.

To talk about a Confederate victory is to overestimate Confederate goals. The South never hoped to actually conquer the North but fought to get it to bargain over terms, to force a settlement that allowed slavery and secession or slavery and re-admission. After the Hampton Roads Conference in 1865, the South knew any settlement allowing slavery was impossible. The whole reason for the War was the South's insistence on being able to own slaves, and WV's departure from VA was over the slavery question as well: western Virginia had a much lower slave population than the rest of the state. With the Wiley amendment to the bill granting WV statehood in 1863, WV agreed to free all slaves who were over the age of 21 on July 4, 1863. Clearly, reunification under the Confederacy would have been impossible with the WV area continuing as free, and the voters who'd voted for abolition in that area would have had to be suppressed, and their vote ignored, in order to do that. As to whether VA expected to "regain" WV: that's a nebulous question: vaguely hope to reunify? were passionate enough to be determined to re-conquer? But all of these would have been thought unlikely to happen during the War.

However, a couple of counties might have voted to rejoin, if allowed. VA did actually sue to regain Berkeley and Jefferson Counties after the War, and was denied. These had been dominated by slave-holders, just like the rest of the Shenandoah Valley, and their vote to join WV in 1863 , held under Union occupation, was perhaps not entirely free. If for some reason the Hampton Roads Conference had resulted in a deal for a seceding Confederacy, it's possible that Virginia would have requested the boarder between WV and VA be adjusted to give it those counties and could have expected that a free plebiscite held on the question would have been in their favor, especially if the newly-freed black residents were not allowed to vote. But as those counties also had important railroad connections, the new government of WV would have strongly resisted, just as it did after the War.