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I have a Playbar, a Play 5, and a Play 3. I also have a record player with a receiver and two speakers that I need to replace. I'm debating either (1) buying a Connect Amp and a pair of nice ($300 range) bookshelf speakers; or (2) buying a Connect Amp and two Play 1s. Goal is to be able to play records throughout the house as well as my digital music and sound from the TV (Playbar and bookshelf/two Play 1s would be in the same room). Thoughts on whether it's better to go with bookshelf speakers or two Play 1s to achieve this goal?
Book shelves vs play 1 really depends on your taste and only you can make that determination.



My question is why you would want to buy a C:A when you already have a play 5.



If your TT and 5 are located in the same room you can leverage the line in jack of the 5.



If not, and this is purely my personal preference, i'll go with a connect (not C:A) and 2 play ones. Manly for the simplicity
Book shelves vs play 1 really depends on your taste and only you can make that determination.



Indeed. Further, a play 1 is also a book shelf speaker, just one with a built in amp and radio. On the other hand there are a range of bookshelf speakers, at a range of price points, with sound quality that is usually, but by no means always, in line with prices.
Question ... do you like the speakers with your existing receiver? If so, there's no reason to get rid of them - loudspeaker design hasn't changed hugely in the last 20 years, after all.
Had no idea that I could hook up my record player (though a preamp) and then into my Play 5. Thanks for that. And if I do that, then the whole set up can be played through all my Sonos speakers? In other words, once the record player is set up through the Play 5, it'll also play through my other Sonos speakers in other areas of the house?
Speakers aren't great and are big. Just need some smaller - and as good if not better - speakers.
Play 1 units will do just fine in that case, and almost certainly will be better once you run Trueplay on them. And yes, the record player will play through any/all of the Sonos speakers that you choose for it to do so.