Everything Centerline said seems spot on. Don't burn the GI Bill $ until you have a couple thousand hours of regional time and are ready to put a 737 type to use.

Another consideration: Since you are retiring, you may possibly be "footloose" enough to go fly a short contract at a foreign carrier. Go see somewhere interesting, make some money and get your experience all at once. If your personal situation is right, it's not a bad option.

One final note (and piece of advice): As you swim your way upstream, you will not be alone. Plenty of other fishies are working hard to accomplish the same goal as you. My advice is to build a genuine network of professional peers. Don't ****** anyone over or burn bridges for short-term gain. This industry is surprisingly small, and you will run into the same folks over and over. One day you might be on one side of the oak desk; next day the tables are turned. If you think you can be a go-it-alone maverick, then you are probably mistaken or are selling yourself short. Some of my best experiences in aviation have been helping aspiring pilots, often relative strangers, get ahead. Don't worry - it comes back in spades!

Your experience sounds fine and you will move ahead quicker than you think, so enjoy the ride!

Best of luck.