I'm considering a UA match. I'm currently Delta Gold and both because of travel patterns and prices, united seems intriguing, despite merger issues. Particularly, I have 4 transcon trips planned (two ticketed on UA, two still unticketed) where UA makes the most sense.


Couple questions:

1) How strictly is the 90 day window on matches enforced?
I have 20k of miles in those trips, enough to fulfill the challenge, but it's 94 days between the first and the last (Depending on how the redeye gets counted it might be 93).

2) Do I have any shot at getting the challenge to start exactly when I want it? It seems like some people have the challenge start quite close to when they contact UA, and others take quite a while.
If they are flexible about the couple extra days, I would want the status to start right near my flight. If they aren't, I can still make the challenge if I skip the first flight and start the challenge mid trip, since that would leave me with 18k of travel in 88 days. Unfortunately this would happen to leave me without status on a redeye.