I have a Masters degree. In architecture. I wasn't necessarily more difficult than the Bachelor part, but was more theoretical a lot of work. Like, tons. Anyway in my field it's a necessity, because it's legally impossible to get your title without it.

Would be better if OP provided more information about his program and school because "Information Technology" encompasses a broad spectrum of disciplines ... (for all we know you could be doing computer science or computer engineering without knowing and getting a masters would be moderately be more advantageous on top of a 4 year engineering degree)

The fact that the army is willing to pay for you to get your masters while covering your school expenses is a massive bonus ...

Free is a relative term, not sure about where he is, but here the military paying for graduate and post graduate education comes with a time based commitment to service, so it isn't really free, it is an investment on their part. In effect they are getting the guarantee of cheap educated personnel as compared to the cost of bringing them in from private enterprise. If he is fully committed to the military already that might be fine, but if not it is something to remember.

I did one, it's in general more difficult than the Bachelors (IT too). If you struggled during the Bachelors, then it can be a bit tough. If you considered your Bachelor easy or at least manageable, then it shouldn't be a problem at all.

I think it trains you well into thinking as a researcher, as a scientist. That's probably the bets thing you get from a Master's or even a PhD. You learn how to investigate and create knowledge by yourself. It's different from a Bachelors, where you are just trained to apply existing knowledge.

Doing a Master's is, in general, worth it. Relatively short, gives you a boost when looking for jobs. A PhD is a more serious decision, but that's not the case here.

In your case, since you'll be paid to do it, it's even better. Will you work during your Master's?

As a developer myself, I would say no it's not worth it in the IT field. My friend did a masters and then went on to do a PhD. During the time he was still at uni, I gained commercial experience which is far more valuable to employers. Getting a masters doesn't automatically give you a more senior position. He started out where the rest of us have and now hes getting the all important experience to better himself. Most jobs only look to see that you've got a degree then move on to see experience / tech you've used. 

What I would say is do it if you feel it would benefit you in some way, but don't do it for employment prospects as generally it means sqwat out in the market.

Sadly I don't possess a pre-formatted academic mind, I'm the kind of person that acquires knowledge in an empirical manner.

So I'm not good with degrees and stuff, school bored me to death to be honest.

Yes, definitely be working while going for my masters.

Masters are only worth it in the hard sciences imo.

Well, it depends on what you want, I guess. My general impression is that the type of work you get with a bachelor's degree in tech is generally extremely boring. A friend of my brother did his bac, got a good job at expedia (80k starting), then dropped it because it bored him to death to go back to do something proper at uni.

I have a masters in math. It gives me lots of options and some job security, but as a teacher that isn’t that hard to have. If I ever did leave the profession, I could easily get a job that pays me double if not triple what I currently make....