This offseason is a pivotal one for the future of the Dallas Cowboys. The team has the ability to have a ton of cap space and they are picking in the top five of the NFL Draft. It also happens to be a time where they must determine what this team is.
Is it a team that is best fit to win under Tony Romo? Is it a team that is built to win under the future quarterback? Because this determination will influence what this team does in free agency and in the draft.
If they see this team as one that is built to win with their franchise quarterback then you can think back to when the Denver Broncos got Peyton Manning. Manning was reaching the end of his career and John Elway and the Broncos knew that when they signed him. In the offseasons following, the Broncos spent big in free agency and put together the team that has been to two Super Bowls under Manning.
If the Cowboys see this team as ready to win within Tony Romo's window, then they better spend in free agency. There will be some players that can really fit nicely in Dallas and they have the cap space if they choose to use it.

The NFL Draft will also vary depending on when they think they are built to win.
If they want to win under Tony Romo, they may be more willing to plug a short-term hole that they didn't fill through free agency. If they want to go long-term then they may take a better player at a position that they have less of a need in.
For example, Myles Jack wouldn't be the biggest need pick, but he's an ultra-talented player and can be a key component for the team for a long time. However, a player like Jalen Ramsey fits an immediate need and can make a major impact now and in the future.

The biggest factor will be free agency. If the Cowboys want to take the true best player available fourth overall then they better fill in the many holes that they have through free agency. There are some major holes on the team and if they are not filled then you really handicap yourself in the draft hoping to fill those needs.
I personally think this team is geared for life after Tony Romo. This is a really young team that has a lot of growing to do. Can they win with Tony Romo? Absolutely they can, but the team as currently composed isn't ready.
If they can handle free agency and the draft well then they can get a team together that can be a serious threat under Romo and beyond if they hit on quarterback.

of the Dallas Cowboys during the Cowboys 39-28 loss to the Atlanta Falcons at AT&T Stadium in Arlington, Texas. Photo by James D. Smith/Dallas Cowboys
I really think there is a potential dynasty brewing here and there are two things that need to happen for that to work out. They need to fill their many holes now if they want to win under Romo and they need to find their quarterback of the future if they want this talented roster to last.