Insurance Claim for Roof + Siding

[Eric La Pratt]

I need a new roof & gutters on one of my buildings. It's an expensive job given the size and height with quotes ranging from $22k - $40k. Additionally, the old aluminum siding on 3 sides (the front facade is new vinyl) has damage but I've not had any interest in redoing it as, in my humble non-insurance adjuster opinion, it is not going to add any value for my rent. This is a long term hold for me that cash flows incredibly already.

What are the pros and cons of having the roofer do an insurance claim versus just paying for it? As others have noted in other posts, it's a situation where I would only need to pay my deductible regardless of what happens - even if they roofer didn't get paid. I would expect some sort of hit on premium and even being dropped. This isn't the only small multi-family I have, however they are on separate policies on different companies but through the same agent. Additionally, one contractor in particular is willing to go full bore and get new siding which, given the size of the building, I am guessing is a $30k project in of itself.

Paying a $1k deductible for $50k-$60k worth of work seems pretty incredible. Is that worth the downstream pain?