Insurance Claims - Should I file one?

[Jacob Compton]

Hello BP Community!
I bought a property recently which ended up having flooding in the basement. I filed an insurance claim to fix and repair the basement. I am now having leaks on my roof. I had a roofer come look at it and he wants to replace the whole roof saying it has a lot of weather related damage. Should I file another insurance claim for this?
I am wanting to buy multiple properties and rent them out. My concern is that I will be dropped by my current insurance or my future properties will have really high premiums due to my past claims. I am using Travelers if that makes a different for anyone.