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I would switch VOO to VTI
He feels guilty earning that extra .7 % with VOO
Coach
I would go for whole number shares. I have never been a fan of fractional shares because they are locked up in the arbitrary rules of your brokerage. If you can focus your efforts for 8-12 months at $5K you may be able get 100 shares so you can sell covered call options on your position. Picking a conservative 0.5% to 1.0% per month return target price could be a nice income source over time. If you ever get assigned you'll have a huge chunk of cash to play on a different index.
Can you explain this more? I just put down the dollar value to DCA without having visibility on price up and downs