I've not had much of the stale, dry, can't open wine experiences as some have posted here. I've only been Diamond about 1.5 yrs, but have had good luck with the f&b.
As for what I take when, I take points on most stays, ssince most of them are 1 to 2 nights max. On stays 3+ nights, I'll take the f&b nad usually have it delivered on the 2nd day. I can drink the wine leisurely over 2-3 days and not bother about feeling like having to dribk it all or try to take with me.