RyanHessan: Your posting certainly has my attention. On one hand I'd like to commend you for realizing that ER is a possibility at age 23. On the other hand, several things in your post really have me worried.
Let's start with food + alcohol, which you put at $850ish/month. Economically, this is a huge expense, and is about 2.5x what my fiancée and I spend per month for two people - and we are notoriously spendy with groceries. For a single person, $300 is more than enough to cook luxuriously and still have enough craft beers in the fridge to have one (or two!) every single day. Then there's the matter of your health - I'm worried about anyone who has more than 5-7 drinks/week. From what you've said I suspect you might be much higher. It's not good for your immediate health and can lead to things that are much worse. Even if you only go with the economical argument, considering your timeline (~17 years to retirement), going down to $300/mo for food and investing the difference could yield you $200k (!) with the historical average, adjusted for inflation.
There's also your chasing of reward-card bonuses. There's nothing wrong with this strategy per-say, but you seem to be putting a lot of work chasing down the 'easy-money', when doing things like cutting your food/alcohol budget (see above) and improving your tax situation (see below) will do you far more good. Plus, with every card your risk of forgetting to pay one goes up, or they change their terms (it happens, often), and your rewards are suddenly not worth it.
On to your savings. The great news here is that you are saving a ton of money for someone so early in your career. But it sounds like you are kind of shooting yourself in the foot with how you are savings. For starters, you seem luke-warm on your 401(k). Your company's options aside, putting enough in to get the match is the easiest returns you will ever get. Many companies only put their contributions in at the end of the year - tha'ts an employee retension strategy - but to you it should make no difference. Also, you make no mention of having an IRA or a HSA. Contributing to these will lower your tax bill and shorten the time til retirement.
now, to address a few of your specific questions:
1. I have no idea what kind of returns I will be looking at in the future? What if in 2030 returns on equities is only 2% a year? What is there's massive inflation? Or what is the structures are all the same but there's another crash? How can I avoid a crash?
2. Because of how my company structures 401K, there's a good chance I get nothing, or very little of the match. Should I even bother with 401K?
3. How much do I need to be safe? How much should I be saving? If I saved $42000 a year would that help me much more than saving $38000?
4. What should my money be in?
5. If I decide to live here long term, should I be trying to buy a bigger place (maybe 3 bed 2/3 bath) and rent out the other bedrooms? Or what? Condo or house?
1) no one has any idea what the return on equities will be for any given year. Certainly not 16 years in the future. But the great thing is that, if you are looking at decades-long time scales, it doesn't matter. First, it doesn't matter because you can't change what happens, so it isn't worth worrying about (see "circle of influence" on MMM), and second your solution to below-average returns is always this: save more. If you want some comfort, look through historical periods going back the last 60 (or even 100+) years. In the last 60 years alone we've had periods of hyper-inflation, 9 recessions, the 'great recession', and about a dozen military conflicts. Even after all of that the average returns, adjusted for inflation have been about 6.8%
2) yes. take advantage of your 401(k). You will get the tax benefit regardless. If you are *certain* you won't get any company match, then max out your IRA and HSA first, then go back to the 401(k).
3). Easy answer to harder question: you need 25x your expected expenses invested in the market to retires. So, if you want to live on 30,000/yr, you need a portfolio of $750,000. If you invested $42k/year you would reach that goal in ~ 10.5 years with market averages (given your existing $50k). If you reduced that to $38k then it would take almost a year longer. if you wanted to "shoot high" and go for $1.5M the estimated time frame would be 16.5 and 18 years, respectively.
4) I'd recommend a low cost index fund. Historically the best rate of return.
5) depends on your market.
hope that helps
N