Have a small collection of less than 100 cds. That I would like to rip them onto my PC, using iTunes, and then wirelessly stream playlists to a device (e.g., Bluesound Note 2) that will connect through my passive Schiit preamp to a Crown 5002 amp driving Magnepan Tympani IVs. 

What devices other than than the Note 2 offer wireless streaming off my PC?  Also, if I use software other than iTunes, which software offers a way to populate my Apple devices, include iPhone SE, iPod and iPad Pro?
With an Auralic Aries mini you can install a hard drive right into the unit.
And as said dich itunes.  dBpoweramp is great ripping software and is more than worth the cost.  
+1 on dBpoweramp. Not only does it do an excellent job in quality, but you can rip to multiple formats at the same time. I do Lossless FLAC and wave. You could also rip to Apple lossey or lossless on one rip if you intend to stay with iTunes. But don't. Too many really good software packages out there to be tied to them. And most interface with Apple hardware well. But be warned, if you have anything of decent quality you play music on, the difference in sound quality between iTunes downloads and your ripped CDs will have you replacing your iTunes collection. Been there, done that. But on just mobile devices, it likely won't.
Thanks for the feedback. I don't download on iTunes and will happily use dbPoweramp for ripping. Is JRiver still the preferred management software, or will dbPoweramp do that too? I only need the Apple format for putting music onto my iPhone and iPod for connection to the radio in my truck.

I was looking at an Olive 4Hd as an alternative to using my PC, but their support appears to be abysmal.

HDTracks looks interesting but used CDs at $2 on average seem a better bargain, even with the lesser sound quality.

Will research the Aries mini.
dbpoweramp is great.

I use Sonos for wireless connection with a server (you can do it to just a single computer if you want) but there are other software packages out there.

I think you will find that you will want to rip a lot more than your own CD collection. Around here, the public libraries lend out CDs you can use to fill the holes in your own collection.