Will waitlists get in my way?

[kreckl]

If I want a resort but people have waitlisted, what are my chances? I can be flexible with days~ but will dates EVER open up? Would it be wiser for me to waitlist? Thinking no because of our flexibility but don't know how waitlist works- if it wouldn't look available on my end because it goes to waitlist first?

 

[ustasmom]

From what I have read, the waitlist fails often. You can waitlist but I'd be proactive, too.