re: What drill set are you getting for the next 20+ years?

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Honestly Ryobi is probably good enough.

I am mostly dewalt but I have been expanding my Ryobi collection. It started with a brad nailer and now includes 3/8 and 1/2 impacts, a rotary tool, shop vac and even a track saw. The Dewalt tools are better... but most of the tools that I picked up in Ryobi are 2X-3X more expensive in yellow.

For a drill specifically good bits makes all the difference. Look into getting some Fisch bits, they are affordable and cut amazingly well.

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I think this is the determining factor.

I'd say Milwaukee is the best quality, followed by Makita and Dewalt in a tossup, slightly ahead of Rigid, with Ryobi next.

Ryobi gives you about 75-80% of the quality, at 50% or less the cost. And they make every fricking tool known to man in that format. I just picked up a Ryobi battery-operated wet-dry shopvac at Home Depot... because it was on sale for $20. Lights, fans, saws, tin shears, 1/2 inch impact wrench, handheld vacuums, every yard tool or gadget you'd never even consider cordless, you can get a Ryobi for probably under $50 most of the time.

Which reminds me, I want a new orbital buffer, surely they have one of those too.