Issues with moving music from my Mac desktop to iPhone

So I'm having issues with getting the music from my Mac desktop to my Iphone. One, my iphone does not connect to it. It does not show it anywhere, and will not allow me to sync it. Tried troubleshooting everything, and talked to a few different support agents to no avail. So whatever, now I'm trying to move my music to my macbook so I can sync it, but I can't find a way to do it. I could transfer through using files and a USB but the macbook has the new USB and I don't have an adapter for it. Plus, even when the music has been synced, it skips over songs even though I have the files and have owned them for years. Kinda just want to get a music specific player and leave Iphones in the past. Any help would be appreciated.

[Re-Titled by Moderator]