Should we stay or should we go?

So, again, I don't have enough time to really write, but I just wanted to get something down. Lately the convo of staying in the Army or getting out is becoming more and more important. It is a really hard decision, so many pros and cons and ifs in every option. Let me see if I can break it down...

We really want to live in Chicago...someday, I would LOVE it! Of course being in the Army doesn't really offer that option, so if we want to live in Chicago now, easy answer, get out, BUT could/would Vinnie be able to find a job? Would we be able to afford a condo/house? (We still have quite a bit of debt) would I be able to get a teaching job that would pay enough to offset daycare in CHICAGO and pay my loans back? I would also need to transfer my teaching license and take at least another test so I can be certified in Middle school subjects..at least social studies. Also, I feel like going this route would get us stuck and Vinnie would probably never get a chance to go to law school like he has always wanted to so that would stink.

We COULD live at home while Vinnie goes to law school, that way we could save some money and I could also try to get a job and get the experience and use my Indiana license which would be a plus. But, we all know how crappy living at home was for me...

We could also get a cheap apartment and Vinnie could go to law school and I could see if I could work, just sucks with the dogs...

Of coarse all the above options involve me going back to work which I'm not totally sure I want to do yet, but at times I really do want to, but I don't know.

So, Vinnie could stay in, this would allow us time to save up money for all the things we want to do...

We aren't sure what the commitment is if he stays in and goes to Captains Career Course, but probably a few years which of course put us at risk for another deployment. I could also start teaching while Vinnie is in the Army, that would definitely help with the debt. There is a lot of "security" with staying in the Army, you can't beat the insurance and other benefits, and I'd be worried about losing all of those things, there is no guarantee of any job outside the Army.

Vinnie wants to apply for a program through the Army that would pay for him to go to law school, problem is they only take about 15 people each year, so it is pretty selective. But, if he were to get in it would be awesome.

well, I'm tired so I'm not going to finish this tonight, but if anyone has any thoughts let me know!