If you're fortunate enough to have a largely free choice over which direction to go, studying wind charts before a ride can become a bit of an obsession. If I'm looking forward to a trip to Ludlow, it can be a bit upsetting when a last minute change in the forecast tells me to go to Devizes instead.
Over the course of a day it's unusual for the wind to remain in one direction at the same strength, so trying to optimise a route to take advantage of the wind can rapidly become quite complex. Sometimes we can have too much information.
In settled weather, it's normal for the wind strength to increase during the day, so riding into the wind first is going to be best. Unless you're Steve Abraham and don't expect to come back until 2am, in which case the opposite is probably true.
If the wind direction is expected to change by about 45º during the day, a common scenario, I'd probably ride out with a cross wind and loop round so that I get assistance on the way back, either clockwise or anticlockwise depending on which way the wind is likely to shift.
On days when the wind is quite significant I might look to do a ride that changes direction a lot, never straying too far from home.
Up to a certain strength (10-12 mph maybe) I find the wind is often less of a hindrance that we give it credit for. I'm sometimes gratified at how easily I'm able to ride into it on the way out, then disappointed at how little help it seems to give me on the way back.