Help me see if going to CS grad school (masters or PhD) could work despite a large debt load

Oh, and to actually answer the question: I think you should try to get an MS while working. It's not THAT hard (many programs cater to part-time students), and is vastly better financially than TAing through grad school (and probably better than most research funding).

I want to go to grad school in order to be able to transition into more technical, more research oriented roles. I currently work in R&D but it's more D than R, and I feel that transitioning into more technical roles will be an uphill battle, despite strong credentials. Why not work for a while, see how much of an uphill battle it really is and, in the meantime, try to find a way to get your employer to pay for it? Grad school will still be there in couple of years and you may be in a better financial position at that point to consider it. Right now, based on the financial numbers you are giving, paying for even the living expenses for the next two years would be financial suicide. The majority of my friends who either went to grad school immediately (and paid for at least part of it) or didn't work for very long regretted that decision, while the friends of mine that waited until they were 30 had their employers help them with tuition and working it around their jobs. The more valuable you are to your employer, the more likely you can have your cake and eat it too.

If I were you, I'd keep working where you are for another two or three years and pay as much as you humanly can into that debt. Maybe even consider living as you would as a grad student - i.e. on 25,000 or so, and putting everything else into the loans. In a few years, your payments should be a lot lower than 700 a month, and going to grad school will hurt less. But I agree with others that you could live on a grad stipend AND pay 700 a month if you were willing to eat ramen, have roommates, and give up all luxuries. Sadly, that's what most grad students have to do.

also, if there are jobs out there that have both loan forgiveness and will help pay for grad school... just something you might consider.

Unless you have other expenses or dependents, the math doesn't add up for me... 1) If you're working as an engineer, is there some reason you can't contribute significantly more than $700/month to paying off your loans? 2) For a fully-funded PhD in CS, assume $24k-$30k/year, depending on departmental funding and outside fellowships. Live cheaply, and keep paying off your UG loans from your stipend. ($700/month would definitely hurt, and my quality of life would take a hit, but I think it would be possible on my grad student stipend). Think roommates, cooking for yourself .... So, how badly do you want this?

Setting aside $700/month as a grad student making $30k is possible if you live frugally and if you're not in a place with a really high cost of living. Also, as a CS PhD student doing distributed systems, you'll have no trouble finding a summer internship. Those pay a lot better than research stipends --- around $6000-$7000/month before taxes.

Yeah, if you are making good money now then it seems like you should be able to pay lot more than $700/month. Have you run the numbers on how quickly you could pay them off if you throw another $500 at them each month? Or a thousand, even better. If you do the math and see that you could pay it all of in X years then it might give you the motivation you need. It would just be so much better if you could start grad school debt free. Also I think you'd get so much more out of it if you had some more years of experience.

I have a masters in CS and I don't recommend getting one. I don't think it actually makes you any more marketable and it costs money (an opposing view: a friend of mine got a masters in CS at a big, impressive school because his undergraduate degree was at a small, undistinguished university and he figured that having "Masters in Computer Science - AwesomeTech, USA" would make him look better. You say you went to a great undergraduate school, so that's out). I'm not saying that a PhD does make sense, but, IMHO, a masters does not.

It sounds like the main constraint is the school debt currently in your parents' names. I'd check to see if you can get Stafford and Grad PLUS loans on top of any tuition/stipend funding you might receive for grad school -- if you can take out new federal loans in your name, you could use that money to gradually "refinance" the debt in your parents' names. The balance transferred to your name could then qualify for in-school forbearance. Once you finish, consolidate your loans and go into an income-based repayment plan. http://ask.metafilter.com/148861/I-have-more-student-loan-debt-than-many-morgages-What-do-I-do#2132341 to another AskMe similar to yours has more info and links on how this might work.