[ThePretender]

If you're taking more than 3 years to rebuild any team to 500+ (including expansion teams), and 4 to make the playoffs, then you should probably restart. What it likely means is you're trying to build entirely through the draft, which isn't the best idea. Some guys you need through the draft, but you need to balance what you get in the draft with what you get in trades as well. And support the core with Rule V, waivers, and smart FA pickups (either low cost vets, or all star to superstar level guys on front loaded deals while you have many players on league minimum salaries).

Really, you shouldn't be doing more than 1-2 years of rebuilding, and a third if necessary to reach the playoffs. It also probably means during your run you sat on your core, instead of trading guys at their peak value and flipping them for prospects to keep the run going. 8-9 years isn't bad, but you should be able to do more if you flip a core player or two every 2-3 years.