wanting to take a digital step

good morning audiogoners, I want to thank you all for your recommendations.  I will be researching the blue sound streamer.  Those Schitt dac's look appealing to get started.  I am excited to hear some music that I don't know about that I will love.  

Or maybe I'll go straight to the streamer but If I do go with the Schitt to start with my laptop what usb cord do I need to connect to dac?  There are a lot of different ones(A-B, etc.) I don't know about, its confusing.  I have a MacBook Air that I was hoping to use.  I think I can use the standard USB port as an audio out but I don't know. I don't want to use the headphone out as the sound was crappola and I had to wiggle the cord to get both channels working.

Again thanks for the help, it is very much appreciated.

Another question about the streamer option, will I be able to stream music stored on my laptop or just from my phone or iPad?

Guys,

Thanks so much again for all the info it is a lot to digest, I have been really digging into this and starting to make sense of it. I really am a digital and technology doofus.  On a fun note I just figured how to airplay send videos from phone of my son do his bmx racing and dirt jumping thing to the TV for large screen post race debrief sessions and showing what he's up to with the mrs.