iTunes Questions

I manage my devices manually, adding and deleting songs onto my iPhone and iPad as I go. I always download songs from my iTunes Match account when I am using wi-fi, (No cellular for Music). It's always worked well, I download onto the HD and delete as I go along. Tonight, I opened iTunes on my Mac and connected my iPhone. Several issues:

1) There are several songs/albums that show up "On My Device" that are not on my device. Those songs play through iTunes, but nowhere to be found on my phone.

2) There are songs/albums that are greyed out. All these songs have the dotted circle next to them, which I understand means they're in the cloud. Why are they showing up "On My Device"? Some of the songs are represented three or four times. One is on my phone, the other two or three are the phantom copies with the dotted circle. Are these phantoms taking up space on my phone?

3) I highlighted all the phantoms, songs that don't appear on my phone and the songs I just wanted to delete. I cleared up a little over 3 gigs. I looked at the Music folder on my phone, and none of the songs that were previously on my phone were deleted. In fact, there are a bunch of songs on the phone that do not show up in the "On My Device" section of iTunes. When I connected the phone, the deleted songs were still on the phone's HD.

4) I can no longer swipe to delete a song from my phone, but when I press the Delete tab on the phone, it asks if I want to delete my purchase. I understand that I can just restore from iTunes, but that seems like a time consuming extra step.

I'm using 8.4 on an iPhone 5S.

Thank you for any help. I understand that iTunes gets more unwieldy with each update, but none of the above makes sense to me. Thanks again.

Andy