Why won't my Mac connect to my iPhone?

I have a MacBook Air and every time I try to connect my iPhone to it, to like transfer pictures or whatever it won't let me. It connects (charging) and just starts going in and out of connection. I thought maybe it was the cord but it works perfectly fine when plugged into the wall. Both my devices are fully updated as well.

When I connect the phone it will tell me I need to download/update something first before having access and when I hit install it says downloading then says it failed because its not available or something,

Super annoying and frustrating, if anyone knows of anything to fix this let me know.

I have an Iphone 8. When people call me and I miss the call, they tell me it sounds like I'm picking up the phone and hanging up?

I have an Iphone 8. When people call me and I miss the call, they tell me it sounds like I'm picking up the phone and hanging up?

Added (1). It appears I do not have a voicemail. I just set up my voicemail, and made a greeting. I tried to call my phone, and my voicemail was not there. It did sound like I was picking up and hanging up, when I was not. How do I fix this issue?

My apple earbuds don't fit?

So i just got an iphone for christmas. Of course it comes with earbuds. The first time putting them into the headphone port, it wasn't fitting all the way. I plugged them into the android and it was fitting and working just fine. I looked in the headphone port, and there's nothing in there.

Added (1). It still doesn't change when I put a toothpick into the port and scrape it.

Should I fix my phone screen or buy a new one?

I dropped my phone last night and I'm debating on what I should do. The screen is cracked on the top but other than that it works fine.
I have a 16gb iPhone 5s and I'm trying to outweigh the good with bad between keeping it or just getting a new phone. I'm also trying to balance the cost between tho two and see which one's more worth it.

Good: I've kept it in amazing condition (up until now lol) for the 3 years that I've had it and even though the screen's cracked, it still works fine. It's processing speed is pretty fast, it still takes nice photos, and it hasn't ever lagged on me.

Bad: Because it's an older model with 16 gb, I'm almost always pretty frustrated that I have no storage room left. The other downside that's been heavily weighing on me is the fact that because it's the oldest iPhone out there right now, I'm worried about when they'll stop making updates for it and I can no longer update it.

Should I just get a new phone instead of fixing my current one?

Did I still get my moneys worth with this new screen protector that is now damaged?

I recently spent $80 for a screen protector for my iPhone XS Max, but I ended up dropping my new phone 3 days afterwards that had caused 2 hairline cracks to appear on my screen protector. My question is, did I still get my money's worth with this now cracked screen protector? I just want to know if I did because I feel like I'm being ripped off spending another $80 for another screen protector.

I also have my previous screen protector which is from the same company and is the same model that I could get them to replace using the new warranty claim from the other screen protector, but that would be immoral. It's also against my own philosophy to be dishonest. My previous one is faulty and has no cracks on it.

Added (1). Both these screen protectors have a lifetime guarantee.