Tenant wants new fence; should I raise rent?

[Dan V.]

I had a tenant move in on September. I offered rent $150 less than other similar properties in community. Reason was because part of fence was down. Tenant understood that. Then Hurricane Irma comes (property is in Miami) and takes the rest of the back fence down too. Tenant wants brand new fence in back. In this rental property, roof fan blew off and shingles came off. I fixed this. And I also resurfaced flat roof. And then after all this, tenants wants a new fence in back for her large dog. 

I have been spending a lot of money. Should I raise rent now or after 1 year contract?