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Invest all at once after maxing out Roth IRA - or each time I contribute?
If you are like most people, your timing is kind of awful.  What I mean by most, is all.  Psychologically we have strong tendencies to buy when the market is high and avoid buying when it is low.  One of the easiest to implement strategies to avoid this is Dollar Cost Averaging.  In most cases you are far better off making small investments regularly. Having said that, you may need to "save" a bit in order to make subsequent investments because of minimums.   For me there is also a positive psychological effect of putting money to work sooner and more often.  I find it enjoyable to purchase shares of a mutual fund or stock and the days that I do so are a bit better than the others.   An added benefit to doing regular investing is to have them be automated.  Many wealthy people describe this as a key to success as they can focused on the business of earning money in their chosen profession as opposed to investing money they have already earned.  Additionally the author of I will Teach You to be Rich cites this as a easy, free, and key step in building wealth.