Re-enlistment vs Private sector

As a very large organization, the military has historically focused on maintaining the right quantity of people who can maintain its standard. That is very different from smaller private organizations who are always trying to find the best possible person for a given job, not just those who can meet a minimum standard.

I don't think it's the right approach, but as long as the military is able to meet its recruitment requirements and its promotion requirements to a standard, it probably will not do much to try to retain specific people. There may be exceptions, but it's how the military has been for a very long time. There is benefits to this approach, but it ends up in some of the best people leaving the military.

Every day there are extremely talented people who decide to leave the military because their skills will be more highly rewarded in the private sector. However, there are also many who decide to stay due to the purpose, mission, and sense of service that they have in the military, and which largely doesn't exist in the private sector.

As a service member, you have to look at the big picture. The amount of Taxable income on you AGI for federal taxes is not a good gauge of how much you make. Further add in the HUGE advantage of Tricare that would cost you, even under ACA, upwards of 1,000 a month. Tack on the retirement pay advantage vs a typical 401K.

Now many of those 300% jobs are based off your "base pay" not the total benefits package and are short term contract jobs that may or may not get renewed.

Yes there is money up front but in the long run, the military wins. You would not believe how many vets I run into that say “I wish I had stayed in, I would be retired today.” I won’t be rich but I do not have to work if I don’t want to. And as someone pointed out Tricare save a lot of money. There is no guarantees someone would make it to retirement but if you consistently apply yourself to the mission, there is no reason they would not.