Keep getting flats. Should I change the tyre?

I bought those conti contact urban tyres in 2023, I cycle the bike almost every day and on some longer rides occasionally, for 2 years I never got a flat tyre. But those holidays have been a nightmare

In the past week I've had like 5-6 flat tyres on the back wheel, almost one every day I use the bike. On the first two I thought it was bad luck but this seems absurd

I posted some pictures from my most recent flats, in this one the hole seemed aligned with one part of the tyre that looks damaged, but it's not always the case

I also posted a pic of some of the damage on the rim, not sure if that can contribute to flat tyres, it's not been a problem before (been like this a while)

So idk I'm just posting for advice. I wanted to change the front and back tyres to see if that was the problem but couldn't because the front wheel is attached with a bolt that is too small for my tool (last pic)

1. Is this kind of tyre wear normal for 2 years? Do people regularly change bike tyres?

2. Do I need to change the tyre? is it likely to be a major contributor to flats?

3. Is there anything else that could be the cause that I should be on the lookout for? I inspected the inside of the tyre to see if a sharp object was stuck there and found nothing

4. is the rim damage something I should pay attention to? Can it contribute to flats?

5. Does anyone wear portable gloves for basic roadside maintenance? if I fix a flat every day I might as well not get my hands disgusting every time

6. Is high tyre pressure better to avoid flats? I only have the portable pump on me so can't really tell how much pressure I have

7. Any advice to avoid flats?