u/ClientPowerful

I'm on the fence whether or not to buy the summer gowild pass, and I'm looking for some advice. Are Gowild routes more likely to be available if I search a week out, two weeks out, one day in advance, etc? Are there any particular airports or routes that are likely to have lots of availability? I'd especially want to use it to fly in and out of Chicago, Denver, NYC, and SoCal, and Mexico or central America, but I'm open to other ideas.

Also, is it more likely to be available if I try to book two one way flights instead of a round trip? How risky would it be in general to book a one way trip to a hub and just hope that a one way flight back emerges before I need to get home?