I think you need to sit down and think about where your loci of control is. A loci of control is that which motivaties you, and it can be extrinsic or intrinsic. For example, an extrinsic loci of control would be: you go to the movies because you find it to be fun. An external source (the fun of the movie) drives you to go see it. An internal loci of control would be you're hungry, so you eat. Hunger comes from inside you, so you then go do something about it.
I say this because for me, it helped a LOT when I found out that I was letting everything external control my drives and emotions. Like, I would let the weather dictate my mood for the day, or I'd let my job determine what I would do on my time off. This kind of loci of control leads to one feeling powerless about one's situation- ie: "I have no control over the forces in my life, so why bother?" Sometimes this attitude is interpreted as laziness by the one expierencing the situation.
So, perhaps you have resigned yourself to your fate- "I can't move closer to my girlfriend because of my job" - your job is then dictating what you can and can't do. Now, I know some of you are going to say "but jobs are important! I need money!" and yes, I'm not suggesting you live in a cardboard box, but you need to perhaps look at your approach to your life. You wanna move closer to your fiancee`? Look for jobs in her area that will get you money, take one, move there, THEN look for radio jobs. Or, call up radio stations in her area to see if anyone's hiring, even as an intern position. You have to take an active role in changing your life in order to see anything change!
I would also suggest that you NOT expect your fiancee` to get the good corparate job to support you while you're looking to break out your radio career. I say this because this can, in a very subtle way, lead to resentment on her part, especially if you have trouble finding a job and become dejected about your chances.
You wanna go back to school? Community college is cheap, and Associates degrees are good on their own in some cases, or at the very least are a good step towards getting a 4 year degree.
You also sound like you're not the best finacially sound person- gambling away your savings and all that. I would suggest calling up your bank and asking if they have free workshops in how to manage your money- if your bank doesn't, sometimes the local library does or a school or university. At the very least, I'm sure there's websites out there that offer good money advice.
Your gambling concerns me, as your response to it- something along the lines of "I know it's bad to be doing this but I like to do it so I do it anyway" sounds to me like you might already have a gambling problem, alebiet a mild one. I would strongly suggest you get to Gambler's anonmous right away- or at least see if you can get some counseling. It might not be what you want to hear, but a gambling problem starts small and then gets bigger and bigger- you owe it to yourself and your future wife to not fall into that slippery slope.
I hope what I have said helps a little- I have definitely been through a period of self evaluation in the past year and it's really really hard to change things when you get into a comfortable rut in your life. HOWEVER, it's THE MOST GRATIFYING FEELING IN THE WORLD when you DO change things and know that it's for the best!!!
