Ok, I have to admit that my first thought was complainypantsing can'tpossiblydoitiveness. However, it did make me think. Thank you for that :)
Of course, after thinking about it, I still can't do it without some combination of living in a cardboard box and a massive payraise.
But, the question has also made me even more determined to save as much as possible without hating life. So, to answer the question 'what would it take', I'll go over some of the numbers that prevent me from doing it, and what steps I can/will take to get as close as possible.
1) My total annual PITI payments are approximately 27% of my after tax income. I do have a roomate, so I've taken that money into account as income. If I impute principal payments as savings, it's still (just) over 20% by itself. And, before anyone suggests that I bought too much house, I bought a house that is about as cheap as it gets for the area, I've recently had to take a 5K paycut, and I am likely overestimating the amount of tax I'll be paying given the amount of pre-tax savings I intend to do, so the percentage isn't too whacky, IMO.
2) Ok, well, that's probably reason enough, but I currently have somewhat of a clown commute that includes tolls which save at least 20-30 minutes per day. My office location has moved twice already, is about to move again, and there's no guarantee that I won't be changing jobs in the near future as well, so moving to be in bike/walk distance is not a good option.
3) While my work does have a 401k, they don't match, and I'm not eligible to contribute until the end of March at the earliest (I might not be able to contribute until the following pay period, so it might be 1 April)
Ok, so those are the biggest challenges. I mean, I just don't make enough money as a single person in a HCOL area in a career field with a relative amount of volatility.
Things to consider (with varying degrees of likelihood):
1) New housing situation. So, if I move near the new office that I know we're moving to, I could potentially save a ton of money as I wouldn't need to take toll roads, wouldn't need to drive as much (hopefully no commute), and would hopefully be able to find a place that would be cheaper (though even if it is it probably wouldn't be by much). Unfortunately, this would mean that I would probably lose my roomate as it would add a good 20-30 minutes to his commute. So, it would have to save quite a lot to make up for that.
2) New job. I've been looking, but I really need to step it up. I have a potential opportunity that would require an international move, but it also pays more and would be a fantastic opportunity, but I can't sit around waiting to hear back on it. So, I will be working on that for sure, but there are no guarantees.
3) I don't think I'm going to be able to quite max my 401k, but I hope to get as close as possible. I've just set up my HSA and plan on maxing that, and I will max my Roth (I know it's not optimal, but I'm really bad at conventional emergency funds, so this will help ameliorate some concerns).
4) I have a number of...let's call it hobby supply related items that I need to sell. That will help considerably as I should be able to get at least 3-5k from them. If I can get off my butt and do that it will make me much more comfortable with maxing my 401k contributions. Any leftover funds from sales can go in my (super tiny) taxable account.
5) Paying off my car will help significantly with cash flow. I plan on doing this by the time that I start contributing to my 401k, so that I will hopefully not have to feel too much of a pinch there.
Well, it's a start. So, thank you very much for helping to get my brain parts working.