We've been sooooo lucky in this draft. First 2 rounds gave been amazing. That being said, you play to win the game. I'll take playoffs over no playoffs every single year.
I mean, it depends on the situation and whether you can macro out and look at the big picture.
Our 1998 team was fun to watch. Chan Gailey came in and revived the careers of the triplets after the stale old offense had left two of them looking pretty bad. Modernized our offense. Fixed our o-line (we gave up only 19 sacks that season, and Garrett took more of them than Troy despite only starting 5 games, so Garrett's inexperience or lack of talent at getting rid of the ball artificially ballooned that sack total up to 19 when it would've been even lower if Troy had played all our snaps). Fixed our draft process, as we were back to drafting useful and good players. And got us on the winning track again.
And at the time, I was ecstatic we were winning again. And wouldn't have wanted it any other way.
But, in the big picture, that year's team still wasn't anything special and wasn't realistically going to win anything. We were in the mode of wanting to eke out every last win we could on the triplet era, so it's not like we wanted to do anything but win.
But... we and the Titans sat there late in the season with identical records. We won our last two games to win the division and cruise into the playoffs. They lost their last two games. Come the 1999 draft, we settle for Ebenezer Ekuban while they get to pick Jevon Kearse, who helped propel them to the Super Bowl. We'd have been better off and better positioned to win something again during the Triplet Era if we'd lost a couple games and been positioned to land Kearse and give our defense that scary weapon to attack opposing quarterbacks.
Having Gailey's first season finish slightly worse would have helped us in a huge way for several reasons. First, it gives us Kearse and better arms our defense for being able to weather the coming modern pass-happy offenses. But also, by dampening the results of Gailey's first year slightly, and giving us Kearse instead of Ekuban in his 2nd year, Gailey's 2nd season would've been more successful than his first and would've created the feeling of momentum and progress (as opposed to him immediately fixing us in 1998 only to take a step backwards in 1999). So perhaps we avoid the franchise-killing mistake of firing Gailey and replacing him with Campo in 2000. We'd have been 1000% better off in both the short-term and the long-term just losing a couple more games in 1998.