Need advice for Naturalisation (good character, police record etc.)

This is to do with the Good Character requirement,

I have had 1 caution in 2017, for shoplifting a a hoodie (£30). I know that this has to be listed on the application and I will disclose it.

1.5 years ago I was caught stealing low value items (I can give details) and was given a
Community Resolution by the police and I handed the items back to the supermarket on the spot.

I'm Unsure about disclosing the second one because I don't know if this is part of my record or not. And the fact that there was no loss, so i didn't have to pay anything back like I did the first time.
I'm wondering if it's necessary to list this for various reasons (such as the fact that it makes me look like a repeat offender, and the fact that it was quite recent - less than three years ago)

I'm very poor and had to take out a loan of £1735 to make the application, if my application is refused I probably won't bother doing it again for at-least 10 years. I want a dual citizenship so I can have 2 passports, allowing me to travel across the EU and places like the Commonwealth

If police stopped you it likely is on your record so the HO will know. And yes it does make you look like a repeat offender, they are both minor crimes, but perhaps it is best to wait for another year before applying and do some volunteering in the community to show your character has changed and you won't reoffend. Hopefully this will also help you raise the money needed for the application and ease your financial situation.

So far, I have read everything about what counts as a record
and I have decided to list the Community Resolution.

When it comes to listing my record, I'll write the basic details of my caution
as that's clearly requested.

And I'm thinking if it asks me to 'list any other thing that might reflect as bad character'
I'll add it to 'other'
and then give basic details about it. Then I'll explain my understanding that it was bad and that I won't do it again. Without making excuses as to why i did it.

From what I read, it's better to be honest, rather than look like I'm withholding information
hopefully it wont be seen as a serious offense

I could say that I went out of my own way buying stuff that I donated to the local community centre, but it probably wont make a difference

I think your approach is sensible. I would still wait for a year and do some actual volunteering in the community to show your character has changed.

I know that before 2023, it was 3 years, that had to have passed since the time of the offense.
I'm just wondering,
how likely is my application to be successful if I apply in September?

We can't comment on that as we are not caseworkers. Given your situation that you need to raise the funds and would probably not bother applying again if you were refused, I would wait for a year and do some volunteering in the meantime, but you are free to do as you choose.