which would you choose

For your Squeezebox, you could get a good quality DAC, like an Ayre Codex for a bit more than $1k, or a Schiit Bifrost Multibit for $400 (both used).
Or, you can buy a Bluesound Node or Node 2.
The Bluesound has a decent (not great DAC), but it is inexpensive and it streams well, and you can add a better DAC if you should like in the future.
B

I use a Logitech Touch into an Ayre Codex with excellent results.  Roon is my software, but LMS works well also.

I use my SB Touch with a Luxman DA-06 DAC. Sounds great even with the free, low rez version of Pandora.