Is it better to wait for a market downturn to do a Roth conversion?
On average, the market will be down 1 year out of 4. 26 of the last 100 years on the S&P were negative. The Roth conversion offers a unique opportunity to convert early in the year, and decide at tax time next year whether you are happy with the result. Of course, if your fund or stock is up, you are likely better off, paying the $1250 tax on the $5000 conversion that's now worth $6000 or more. If it's down, you can recharacterize. The volatility of the market helps makes this process more attractive. If my converted shares dropped quite a bit, the recharacterization is far more desirable than a small drop or no drop at all. Of course we don't wish for that drop, any more than we wish for our house to burn down to make our insurance pay off.  To be clear, you'll benefit from a conversion she the market goes up. The downturn only lets you reverse the bad move.
Except I would never keep 10k in cash inside a Roth unless I was waiting for a buy opportunity.  Money in a Roth should be invested, not sitting in cash, you're not taking advantage of any of the features of a Roth by leaving it in cash. The primary advantage of an IRA or 401k is you get taxed effectively one time on the money (when you contribute for Roth, or when you withdraw for Traditional), whereas you get taxed effectively multiple times on some of the money in a taxable account (on all the money when you contribute, plus on the earnings part when you withdraw). Of course, you have to be able to withdraw without penalty for it to be optimally advantageous. And you said you want to retire decades early, so that is probably not retirement age. However, withdrawing early does not necessarily mean you have a penalty. For example: you can withdraw contributions to a Roth IRA at any time without tax or penalty; Roth 401k can be rolled over into Roth IRA; other types of accounts can be converted to Roth IRA and the principal of the conversion can be withdrawn after 5 years without penalty. You will owe tax on all but the deposit that was not taxed.  e.g. You deposited $5000/yr for 3 years, and deducted $5K for each of 2 years (the third $5K  deposit was a nondeductible IRA contribution which you reported to the IRS by filing Form 8606 with your tax return for that year). Now you convert the total balance of $18K ($15K of contributions plus $3K of interest/gains). In this case, $5K is not taxable income while the $13K is taxable income. This calculation is done on Form 8606 for the year of the rollover. Edit in response to OP's comment. The Roth conversion is text based on the value of a day it was  converted. One thing to be aware of is that you can re-characterize up until the time you file your taxes for 2017 in April 2018 (or with extension up until October).  This offers you the opportunity to undo the conversion if for whatever reason the value is lower at the time you do your taxes or if the converted amount will put you into a higher tax bracket. You don't need to give the IRS a reason, it's up to your discretion. As Dave note in a comment, the conversion isn't all or none. The recharacterization, along with this fact, help you to fine tune exactly how much in converted in hindsight. I don't like your strategy.  Don't wait.  Open an investment account today with a low cost providers and put those funds into a low cost investment that represents as much of the market as you can find. I am going to start by assuming you are a really smart person.  With that assumption I am going to assume you can see details and trends and read into the lines.  As a computer programmer I am going to assume you are pretty task oriented, and that you look for optimal solutions. Now I am going to ask you to step back.  You are clearly very good at managing your money, but I believe you are over-thinking your opportunity. Reading your question, you need a starting place (and some managed expectations), so here is your plan: Now that you have a personal retirement account (IRA, Roth IRA, MyRA?) and perhaps a 401(k) (or equivalent) at work, you can start to select which investments go into that account.  I know that was your question, but things you said in your question made me wonder if you had all of that clear in your head. The key point here is don't wait.  You won't be able to time the market; certainly not consistently.  Get in NOW and stay in.  You adjust your investments based on your risk tolerance as you age, and you adjust your investments based on your wealth and needs.  But get in NOW.   Over the course of 40 years you are likely to be working, sometimes the market will be up, and sometimes the market will be down; but keep buying in.  Because every day you are in, you money can grow; and over 40 years the chances that you will grow substantially is pretty high.  No need to wait, start growing today. Things I didn't discuss but are important to you: For #1, I see no advantage in putting money from your non-retirement savings into a Roth just for the purpose of using it as a down payment on your house.  Why not just put the $5.5K directly toward the down payment? For #2, dollars converted from a traditional 401K or IRA to a Roth are considered income, and will be taxed at your marginal rate.  So if your marginal tax rate is 25%, you will need to pay $5K in order to convert the $20K.  Usually this payment is done independent of the conversion amount--in other words, you would convert the full $20K but pay the $5K in taxes out of other funds (checking/savings). Based on your stated goals of using the money for a down payment on a house, I don't see any advantage to contributing (or converting) to a Roth IRA. I know this is heresy but if you have funds for significantly more   than 6 months of expenses (let's say 12 months), how risky would it be   to put it all into stock index funds? Quite risky as if you do need to dip into it, how fast could you get the cash? Also, do you realize the tax implications when you do sell the shares should you have an emergency? In the worst-case scenario, let's say you have a financial emergency   at the same time the stock market crashes and loses half its value.   You could still liquidate the rest and have sufficient funds for 6   months. Am I underestimating the risks of this strategy? That's not worst case scenario though. Worst case scenario would be another 9/11 where the markets are closed for nearly a week and you need the money but can't get the funds converted to cash in the bank that you can use. This is in addition to the potential wait for a settlement in the case of using ETFs if you choose to go that way. In the case of money market funds, CDs and other near cash equivalents these can be accessed relatively easily which is part of the point. A staggered approach where some cash is kept in house, some in accounts that can easily accessed and some in other investments may make sense though the breakdown would differ depending on how much risk people are willing to take. If it truly is an emergency fund then the odds of needing it should be   very slim, so why live with near zero return on that money? Something to consider is what is called an emergency here? For some people a sudden $1,000 bill to fix their car that just broke down is an emergency. For others, there could be emergency trips to visit family that may have gotten into accidents or gotten a diagnosis that they may pass away soon. Consider what do you want to call an emergency here as chances are you may not be considering all that people would think is an emergency. There is the question of what other sources of money do you have to cover should issues arise. $23,000 Student Loans at 4% This represents guaranteed loss. Paying this off quickly is a conservative move, while your other investments may easily surpass 4% return, they are not guaranteed.  Should I just keep my money in my savings account since I want to keep   my money available? Or are there other options I have that are not   necessarily long term may provide better returns? This all depends on your plans, if you're just trying to keep cash in anticipation of the next big dip, you might strike gold, but you could just as easily miss out on significant market gains while waiting. People have a poor track record of predicting market down-turns. If you are concerned about how exposed to market risk you are in your current positions, then you may be more comfortable with a larger cash position. Savings/CDs are low-interest, but much lower risk. If you currently have no savings (you titled the section savings, but they all look like retirement/investment accounts), then I would recommend focusing on that first, getting a healthy emergency fund saved up, and budgeting for your car/house purchases.  There's no way to know if you'd be better off investing everything or piling up cash in the short-term. You have to decide how much risk you are comfortable with and act accordingly. "If I buy property when the market is in a downtrend the property loses   value, but I would lose money on rent anyway. So, as long I'm viewing   the property as housing expense I would be ok. This is a bit too rough an analysis.  It all depends on the numbers you plug in.  Let's say you live in the Boston area, and you buy a house during a downtrend at $550k.  Two years later, you need to sell it, and the best you can get is $480k.  You are down $70k and you are also out two years' of property taxes, maintenance, insurance, mortgage interest maybe, etc.  Say that's another $10k a year, so you are down $70k + $20k = $90k.  It's probably more than that, but let's go with it... In those same two years, you could have been living in a fairly nice apartment for $2,000/mo.  In that scenario, you are out $2k * 24 months = $48k--and that's it.  It's a difference of $90k - $48k = $42k in two years.  That's sizable. If I wanted to sell and upgrade to a larger property, the larger   property would also be cheaper in the downtrend. Yes, the general rule is:  if you have to spend your money on a purchase, it's best to buy when things are low, so you maximize your value.   However, if the market is in an uptrend, selling the property would   gain me more than what I paid, but larger houses would also have   increased in price. But it may not scale.  When you jump to a much larger (more expensive) house, you can think of it as buying 1.5 houses.  That extra 0.5 of a house is a new purchase, and if you buy when prices are high (relative to other economic indicators, like salaries and rents), you are not doing as well as when you buy when they are low.   Do both of these scenarios negate the pro/cons of buying in either   market? I don't think so.  I think, in general, buying ""more house"" (either going from an apartment to a house or from a small house to a bigger house) when housing is cheaper is favorable.  Houses are goods like anything else, and when supply is high (after overproduction of them) and demand is low (during bad economic times), deals can be found relative to other times when the opposite applies, or during housing bubbles.   The other point is, as with any trend, you only know the future of the trend...after it passes.  You don't know if you are buying at anything close to the bottom of a trend, though you can certainly see it is lower than it once was.   In terms of practical matters, if you are going to buy when it's up, you hope you sell when it's up, too. This graph of historical inflation-adjusted housing prices is helpful to that point:  let me just say that if I bought in the latest boom, I sure hope I sold during that boom, too!"