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Complex Question(s)...imo, the 20s on those wheels look great. That said, you will be hard pressed to get more than 25/30k miles out of them. As to the one set/size of tires that will work well or "ok", for your very extreme potential driving conditions, (albeit infrequent severe situs), 20s aren't "it".
Even 20s in an "all weather" tread are not going to be fun for the potential weather you might encounter on that winter run to TN,NC & VA...but, you might get lucky. I personally wouldn't want to run serious snow tires or, maybe even swap wheel sets&dedicated snows, just for a couple weeks of "winter weather". As for the rainy season in OKC, I would not worry about 20s, other than their tendency to hydroplane due to tire width.
You may get more opins, but if that wheel/tire combo are what you & your wife really like, I'd go for them. If you lived in MN or another serious winter state, I'd rec'd hunting up a set of 19s/18s with dedicated snows for the few months you might face real winter driving conditions.
Long ramble and not sure it is of help...
GL,mD
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