Hard to say, upgrade means going to a junior base which are almost universally high COL areas and you'd need to either move there or rent a crash pad for several months to several years until you can go back.

In my case, I'm lucky enough to have 0 ex-wives and no kids to put through college so I'm in a comfortable position money wise. It would take a pretty big chunk of money for me to take the hastle to upgrade until I could hold my base.