Ok, maybe I'm not good at math, but here's the numbers I put in ol' calc.exe (where you gave a range, I averaged it out):
$630
$272
$112
$475
$240
$125
$8
$5 (you didn't give a figure for your wife's prepaid, so I made one up)
$45
$32.50
equals $1,944.50/mo, * 12 months = $23,334/yr
Is your $50-$60k/yr pre or post-tax (with three kids, I'm guessing both numbers are fairly close)?
Some important/essential numbers I think you're forgetting are insurance (health, house, and car), car maintenance (include regular maintenance like oil changes and new tires, irregular maintenance like the inevitable new transmission, and somewhere you need to add in registration fees), property taxes, things like that. I'm sure that'll bump up your numbers a decent bit. Even still, I'm guessing that all the "essentials" are only costing you around $26-$30k a year. That gives you between $20-$34k/yr extra, WITHOUT changing any of your current essential spending (i.e. no trading in the truck, driving less, reducing grocery bills, etc.)
The non-essentials are what's really getting you now. You need to sit down with at LEAST a month's worth of expenses (three would be better, six months would be pretty darn good) and see where all the money's going to. Family of five, it's REALLY easy to spend $50/wk on going out to eat, without even trying. Heck, one trip to McDonald's can wipe out half of that. $50/wk times 52 weeks = $2,600. Even if you're currently spending $100/wk, if you get that down to the "extravagant" $50/wk figure, that's still $2,600/yr in savings.
Careful on all the clothing "savings". $2 for a pair of pants...are ALL the clothing bought that good of a price? Or just an example of how good it CAN be? If there's piles and piles and piles of clothes everywhere, and you're donating a bunch of stuff because it's hardly been worn...you're buying too many clothes.
Here's what I would do:
#1, track those expenses. See what you've been spending money on, decide what you WANT to be spending money on, and come up with some kind of budget. You don't have to budget every single thing; I mainly budget items that can easily get out of control (we didn't budget groceries at first, until the spending ballooned to $150/wk; now we're down to $90/wk).
#2, give the kids an allowance. Break it down however you want (we do 40% spend, 30% save, 20% invest, and 10% donate). Oldest kid could have a clothing budget as well. Now this is important...give them the money, let them spend it on whatever they want (long as it's legal of course...for clothing you'd make sure the bare minimum required for school is purchased, but let them decide whether to spend $200 on shoes and 50cents for jeans at the thrift store). And DON'T BUY THEM CRAP throughout the year; birthdays can be a cake and a SMALL present, Christmas can be a bit more (we probably spent under $10 per kid for Christmas, though my mom spent more like $100). If they want something, tell them "sure, if you have the money..." Yeah yeah, many will say "you shouldn't give kids an allowance not tied to chores" or what-not...but if you're buying them stuff all the time, what's the difference?
#3, reign in the dining out spending. I'm 96% sure that's a big part of your expense. Set an amount, and as long as the spending is kept under control, no need to feel guilty. So if you budget $50/wk, then go to McDonald's twice a week, or that fancy restaurant once every two weeks, or whatever. Don't feel guilty about the money spent on it, though you should regularly sit down and rethink your priorities (and decide if the eating out budget should stay the same, be increased, or decreased).
#4, if you get that $10k bonus, dump it straight into a Roth IRA. Don't depend on that money. In fact, you should be walking around for a few weeks with a dazed look on your face, cause you're not sure where to put that bonus (because hopefully you can eventually increase the 401k savings, AND contribute regularly to your Roth IRA, so the $10k will actually be somewhat "unexpected"). FYI, the contribution limits for Roth IRAs have increased to $5,500 per person; so a married couple can put in $11,000/yr total.
Rough estimate, I say it'd take you about a month to really come up with a plan and execute it. Three months after that, I think the truck would be paid off. Another five months should see the student loan vanquished. So within 9 months, you can be free of all non-mortgage debt and have $10k+ in Roth IRA accounts; what a great way to start the new year! If you really buckle down (reduce grocery spending to $400 or less a month, trade in truck for cheaper more fuel efficient car, reduce electricity costs, etc.) then you could be there by this Thanksgiving; now that's something to be thankful for!
Oh, on burn-out and wanting to move around and make more money; I'm assuming (possibly incorrectly so) that there's something like a "travel IT guy"? Where you can take a 3-6 month contract somewhere, really make bank, and then move on to the next? I dunno...but I know there's such a thing as travel nurses, and it can be a good way to see the country and make some money at the same time. If you can get contracts in a high cost of living place like Alaska, and live the rest of the year in a low cost of living place like Kentucky, you're doing pretty good.
Edit: To keep track of our budget, I use eeba on our Android phones (there's an iphone version as well). Whenever we spend something that's tracked (groceries, going out to eat, our misc money) we put the amount on our phone. They sync with each other, so if I spend $50 on groceries in the morning, my wife will notice when she tries to go out that evening after work. To look at the "big picture" I'm trying out YNAB. It's not quite setup the way I'd want, but it does make it easy when my wife asks about account balances and I can just fire it up. Can be a good motivation to not spend once you've reached a certain milestone (i.e. once your net worth hits $50k, you want a good cushion before you make a big purchase, cause you don't want it to fall back to $40k-something).
