What is the best way to play music with DAC/wireless?

Hello, I (an old fool just getting out from cd) have basic questions for digital format.

I have Aiff format songs stored in Mac/iPad/iPhone.
I play them by using app called Flacbox.

My question is, what is the best way to play these song?

1) DAC - Amp
This is my basic idea, for example, iPad/Macbook connected to DAC via USB cable then to amp.

2) DAC - Amp
Using USB thumb drive to DAC unit then to amp. Honestly I don’t know what advantages this method have over method #1

3) Streamer - Amp
Using Airplay from iPad/Mac wirelessly with Streamer then connect a streamer to amp via cable.

I do not want to pay any kind of subscription service (though it has a free version). I want my system to be closed one without internet connection. (Only using router)

For method #1 and 2, I consider ARC CD6 and PrimaLuna Evo 100 Dac. No idea what would work better.

For method #3, I have no idea what models are equivalent to models I mention above. (Good DAC with Airplay support) Most of them focus on streaming service that I do not want. Also not sure which one can work out the best with Airplay. (Only wireless solution that I can use free. I feel like airplay is still better than bluetooth.)

Please share experience and advice how I can get the best sound quality. Also if you have any model recommendation, please share some wisdom, especially airplay supporting one. 

Again Please feel free to educate me. Thank you.