Further to the above post, the Oilers didn't "blow up" the team until after the 2008-09 year. Prior to that Lowe was doing a terrible job of trying to build the team on the fly, similar to what Calgary's been doing (they totally missed the playoffs better than us!). So we're 3 full seasons in to the rebuild now.
Let's look at Chicago: http://www.hockey-reference.com/teams/CHI/
Playoff team in 2002. Missed by a fair amount in 2003, and blew up the team. Terrible finishes from 2004-2007 as they rebuilt and stocked draft picks:
2003: Seabrook, Crawford, Byufglien (245th!!)
2004: Barker (lol), Bolland, Bickel, Brouwer;
Note that they actually didn't pick particularly high until the last two years of their rebuild, or the end of their 3rd and 4th full seasons of rebuilding. They did not make the playoffs until the 6th year of their rebuild, or 5 straight years of non-playoff hockey. They won the Cup in the 6th year.
Pittsburgh's rebuild started at the end of the 2000-2001 season (oddly, they made the playoffs that year, but that was the last year Jagr played for them). They were awful for 4 straight years. They didn't make the playoffs for 4 straight years, and it took them 7 years from the start of their rebuild to hoist the Cup.
The Oilers right now are arguably in a similar position to where Pittsburgh was at the end of the 03-04 season, or Chicago was after 06-07. Meaning next year we'll fight for a spot in the playoffs but likely not go deep, the following year we should easily make the playoffs, go deep but get eliminated, and hopefully the 2-3 years after that provided we can keep the core together and build a good supporting cast consistently challenge for the Cup, if not outright win it.
Or we might end up like Washington. Or the Islanders.