Since you asked for opinions... I'll give my 2 cents. Pay off some of your current truck, first. You will be upside down on payments if you try and sell it or trade it in because you owe so much on it. You said you are possibly looking at a new career... wait until you get there to see what your income will be and what expenses you are going to have. You mentioned baby fever... let me tell you, that **** is expensive!! I have an 8 month old and it will drain your pockets. But, it is SO worth it! Your living arrangements will become a factor (apartment/house, own/rent). End the end, it all comes down to what you can afford each month.
Figure out how much of a payment you can afford, if you are going to get a loan. Go to your bank, or a credit union, and get pre-approved (shop around for the best interest rates). That way, you know your budget and what your payments will be going into the dealer. The dealer will ask you what kind of payments you are wanting... don't fall for that. Tell them you are looking at "out the door" price, nothing else. They will arrange payments however they want, if you finance through them, to get you in a truck that is out of your price range. Go through the paperwork with a fine tooth comb. Look at ever number they write in. They will try and slip "add-ons" onto the final number as fees, or whatever, just to up the final price.
Also, really sit down and figure out what type of truck you "really" need. Do you really need a 2500? The new 1500's are very capable at hauling/towing for the average person. If you need the 2500... no problem, just make sure you really do. With a baby in the future, you'll want the Crew Cab. Research what options are available and what you want. I had salespeople that didn't know anything about the trucks and try and tell me what options were available or not, which was mostly wrong.
Sorry that was so long winded... just trying to help.
