Will filing multiple claims for roof hail damage affect my ability to get insurance on properties in the future?

[Charles Mangum]

In 2013 I had two claims at two different rental properties of mine for hail damage. I have a house now that I'm going to put up for sale in October. It clearly has hail damage on the roof. It is probably about 15 years old. It looks good pretty good (that is it's not ugly worn out). I'm assuming if I replace the roof it will be a more valuable property. My concern, however, is that if I have another claim it might make it might be difficult to find insurance for properties I intend to buy in the next 6 months.

Any guidance / experience here? What would you do- file the claim and replace the roof or sell it with the current roof?