Strictly from a roofing system, weather protection standpoint, a pitched roof is much less likely to encounter leak issues, unless it is damaged by outside forces (think hail, high wind, tree limbs, etc.).  

For those that don’t live near there properties, how do you know if you need to call the insurance agent if there was hail or another weather event

Could be in a flood zone, a 100 year flood zone, high crime, freakishly prone to hurricanes, hail storms etc. 

In a place like Texas where I live there tends to be severe weather and frequent storms so raising your deductible for wind/hail to save on premium might not work out.  

There's a whole separate insurance for tornadoes, called Wind and Hail coverage. 

Wind and hail insurance is required on top of standard homeowners insurance.

Had an alternate roofer inspect and he indicated the roof is in good shape, no hail damage anywhere and he doesn't feel like these shingles will cause any issues, HOWEVER, my issue would be getting someone to insure it (as it is)..last thing i want is 5yrs from now there is damage and the claim folks get on the roof and see all these shingles with lines through them and not cover the damage.As a new investor/home buyer -- any suggestions on my next move here?

Had an alternate roofer inspect and he indicated the roof is in good shape, no hail damage anywhere and he doesn't feel like these shingles will cause any issues, HOWEVER, my issue would be getting someone to insure it (as it is)..last thing i want is 5yrs from now there is damage and the claim folks get on the roof and see all these shingles with lines through them and not cover the damage.As a new investor/home buyer -- any suggestions on my next move here? 

Had an alternate roofer inspect and he indicated the roof is in good shape, no hail damage anywhere and he doesn't feel like these shingles will cause any issues, HOWEVER, my issue would be getting someone to insure it (as it is)..last thing i want is 5yrs from now there is damage and the claim folks get on the roof and see all these shingles with lines through them and not cover the damage.As a new investor/home buyer -- any suggestions on my next move here?

Turns out, there was hail damage - and insurance paid for the entire roof.