Hi David97,
As gob11 mentioned, there is no "good" time.
When I started along my path in '99, times were relatively good. I was in a position in late 2001 to get my first job and times were still good as I sent out resumes. That all changed in the matter of a couple of minutes on September 11th and the deflated industry continued for a number of years. What would have been flying job offers in August and early September were ramp job offers from late September, if offers were even given.
In a similar way, the industry can be deflated for years and then in the space of a week or two airlines are hiring tens to hundreds of pilots.
A seven-year cycle is what I'd always been told, and 17 years in I see that this stays relatively true: seven "good" years followed by seven "deflated" years.