This is actually a good strategy to use well before things get to the going-to-court state - shoddy record keeping is certainly not unique to shady debt collectors (I speak from experience), so while I wouldn't advocate this as a way to get free money (as a different person in the Ira Glass interview is described as doing), if charges/interest amounts don't look right to you, say something about it. Possibly repeatedly, and in the face of aggressive guilt tripping from the billing department.
@jquick I use tweezers, and I have crazy thick eyebrows. But, I don't go for the pencil-line-thin look, which I could see being tricky to get on your own. That said, I also don't really do the salon/beauty treatment thing (makeup is for special occasions like weddings, and I get my hair cut every year or so), so maybe I just look unkempt and don't know? Sounds like I save a bundle by my obliviousness, though.
Assuming the $500 in option 3 is an annual thing, I would vote for option #3. If everything goes right, you save over a thousand in deductible/HSA spending. But suppose everything goes wrong: for plan #1, you pay 500 - 2000 dollars. For plan #3, you pay 2250 - 4000. But if you adjust for the deductible/HSA savings (1222 + 500), plan #3 actually becomes $528 - $2278. Which means if you have no major health issues, you'll save $1700 on plan #3 vs #1, and if you do have a major health issue, you'll spend $28-$278 total more on #3 vs #1. If you can average this over a few years, then even with a major health issue in 4 out of 5 years, you'd come out ahead on plan #3. If you're expecting health issues, though (pre-existing conditions, planning on pregnancy/wisdom teeth removal/etc), #1 probably makes sense.
+1 to take the promotion, apply to grad school (start working on the application now), and leave in 10 months. Think of it this way: at the moment, your company has no one except you ready to jump into this position. If you take the new job, you have 10 months to find and groom a successor who can then take over for you when you leave. You'll be leaving your co-workers in a way better position then they currently are, and you'll be in a better financial position, particularly if you keep the roommates. Bonus: if you dislike having the roommates, keeping them will help stave off some of the complacency you're worried about.
I've used a realtor twice (once buying, once selling) and bought once without. Not using one saves you money, even if the "seller pays", since the buyer is the one putting the money on the table. If you can say to the seller/seller's realtor 'look, you net 3k/6k/9k more out of this because I don't have a realtor that you have to pay 3% to', that makes your offer more attractive than an identical offer from someone with a realtor. And while I always read all the fine print, I found not having a realtor made me follow up with folks with even more detail, and prevented a couple of snafus. I would never use one again for buying. For selling, on the other hand, I adored my realtor - I was pretty busy with other life things, and she did all the staging/sprucing up/photos/open houses/etc without me needing to lift a finger (she also gave me cookies). She nearly paid for her commission in what she saved me by knowing people in the business and getting good deals.
@Theestablishment Care to elaborate? I've done this at a couple different jobs, and it's information I've been glad to have every time. One place, I was making less than a coworker, but not by a lot and for totally understandable reasons. Another place, I was making less than someone in the exact same job, who had started at about the same time as I did. I got to find out 2 things: (1) HR/recruiting lied through their teeth about what the salary bands are and (2) it doesn't matter if you don't want to work there, or if the offer isn't competitive, get an offer from another company for negotiation leverage. These are extremely useful facts for negotiating raises.
Having interviewed several hundred people over the last couple years, I totally identify with this - one thing I've found helpful, if the candidate is nervous, is to patter a little at them to give them a moment to calm down, and maybe ask them some very easy questions ('would you like a bottle of water, or anything else to drink?' easy) just so they have a chance to say something and have it be ok. Smiling and nodding also helps. I have not, however, figured out a graceful way to handle requests for feedback - I have no idea what legal/PR issues I might be creating, and I'm bad at giving constructive feedback under the best of circumstances (plus, the interview is really not set up for me to figure out how the candidate might improve, it's to evaluate what skills they currently have, so my feedback would pretty much be limited to 'be more knowledgeable/proficient in this field/the specific topics I asked you about', which seems unnecessarily mean and unhelpful).
IME, having done both, I'd much rather have a 60-hour/wk job I really love, than a 30-hour/wk job that's kinda boring. Maybe 16 hours/wk would be low enough that I'd be ok with it? For me personally, though, spending a large chunk of waking hours (a) in one location, so no long travelling/projects, and (b) working on something that I can't really get into, because I'm only working on it for a few hours each day, is actually pretty not-fun. Maybe the point is that most jobs aren't interesting anyway, so at least we could try to do less of them? That's a pretty depressing rallying cry, though, I can see why it hasn't caught on.
Best craigslist find was a full bedroom set for $85 - the sellers were re-doing their guest room and just wanted to be rid of the furniture, and I as a recent grad needed all of it. Bed frame, box spring, mattress, night stand, and dresser, all of which have now survived 3 moves and nearly a decade of use. This was before the bedbug outbreaks, though, so I'd probably be more leery of craigslist mattresses nowadays.
@jquick I actually view not having to care what others think as a remarkable privilege of my line of work - if I were in another field, I would probably spend more, because the opinions of clients and bosses is actually very important. Striking it rich is called making 'f*ck you' money for a reason... I think the one insight I could provide is that being able to avoid a scarcity mindset around money is actually really helpful for spending less - because I know I have the option to buy thing X later, it's less important that I buy it now, which helps me spend less overall. The other, less-generally-helpful, motivation is that I have hoarder tendencies, and the best way to keep them at bay is to just not have things in the first place =).