A pair of Sonos Play 5 Gen1 or a single Sonos Pay 5 Gen2, which option sound better?

I would go with the single Play:5 (Gen 2). You will get better stereo separation with two Gen 1s, but the Gen 2 is just a better-sounding speaker with deeper bass, more clarity, and a smoother sound. Plus the Gen 2 just looks better and is compatible with AirPlay.

The Gen 2 is also compatible with the Sonos S2 app which will be useful if you decide to add newer speakers to your Sonos ecosystem in the future.

It depend on what you are accustomed to listening to, because that is what will sound better to you. If you are used to listening to stereo music, via a well placed pair of speakers, that is what will sound better to you.

If not, it may be the single 5 gen 2, but even there it may be a toss up. 

From the price point where I am staying, 2 x Play 5 Gen1 cost less than 1 Play 5 Gen2, both used, hence, I am very tempted to get 2 Gen1. I am a hifi nut and have a huge vintage system in my living room and looking for 1 system in my bedroom to play some music and use it to jam along with my cajon (box drum) and ukulele.

I have searched in youtube hoping someone uploaded a AB comparison for these 2 options but can’t find any. There are a few AB comparison for both single piece where Gen2 is mile ahead in every aspect of the music. With 2 x Gen1 we could expect, mid and low freq should get louder, stereo imaging should be better as well. Just hope to listen to one AB comparison or have anyone here have done so?

Louder - a little, but the stereo imaging of a pair of correctly spaced speakers can’t be touched by the single speaker. And for many, that trumps all else as long as the stereo pair is of decent quality - which the original 5 is.