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The next $1000 I put into my retirement accounts is no different than your first $1000.

No, its absolutely not "worth" it to "wait and see" unless you have proven clairvoyance. Just invest for the future when you have the money to invest - stock market should be for the long term.

On average, buying now is cheaper than buying later. And you can't time the market.

You're going to be contributing to this for years and years, so where the market was at when you invested your first dollar will be meaningless.

Time in market beats timing the market.

True, but time in market with educated and not naive timing beats "time in market". Edit: "naive", and that I simply mean to time ETF payments with awareness and possibly technical indicators.

Minimum 3 months of savings, pay off high interest debt, and max out 401k or at very least max out your employer match. Max out employee stock purchase programs and sell quickly.