Congrats on your decision. I really enjoy the Pono and I'm sure you will as well.
Yes, you can drag and drop files from your computer to the Pono, or directly to the micro-SD card. Pono also provides a music management package called PonoMusic World. I find that this tool is easy enough to use that I usually use the tool instead of directly doing drag and drop to the device.
Most of the answers to your questions can be answered by reading their FAQ and watching their videos.
https://www.ponomusic.com/faq
https://www.ponomusic.com/contactus
Good luck!
