Not entirely sure where this belongs. But wanted to share.
I have a handful of Wemo outlets around the house that work fine. And and EcoBee thermostat.
I have a dimmer switch for the lamp over my desk. Over the weekend I switched it out for a Lutron Caseta dimmer using the $99 kit that comes with the switch and hub. Everything worked the first try, hardware and software. No issues getting it talking to HomeKit. Going to do another switch later this week.
I was tempted to go with more Eero switches but after googling and asking around I got the vibe that Lutron was a more reliable option.