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I have a 10+ hear old Play 1 using the S1 system. I am considering purchasing an Era 100 for a stereo setup with voice control.

Can I expect that setup to work resonable well or is it a bad idea?

Sonos only lets you stereo-pair two of the same speakers: Play:1 with Play:1, One with One (or One SL), Era 100 with another 100 etc. 


Note too the Eras are S2 only so you’ll need to upgrade your system and move the Play:1 to S2. 
 

There are other apps that may let you create these two as a stereo pair; how they’ll sound I can’t say.