Do I put a low deductible on my wind/hail and then use insurance to pay for a new roof once it fails? 

Hail is the bigger issue in my opinion. 

These are Visio, LendingOne, @Timothy Hero as broker for a portfolio loan on 8 properties (if I remember the number of houses correctly) followed by a STR purchase, and I used Sortis for short term bridge financing on a property that was hit by hail while under the contract period so we had to switch to a different product until we fixed it up.

Also there are weather issues with Indiana winters and pipes possibly freezing, thunderstorms and hail damage2) Knowing how long to hold onto a property, 1031 exchange it to another property or DST, or in some cases sell it and pay the small capital gains tax (if any) to have less headache. 3) Underwriting the deal incorrectly (factors: local appreciation, rate of rental increase, economic growth, gentrification of area) and being overly optimistic (a renovated 100 year old home is still going to have problems).

With the Midwest there are also winter issues and hail damage from thunderstorms that we don't deal with in California.

Losses due to wind, hail and other forms of disaster are becoming more and more frequent.

. :)  Keep in mind, that YES they are more expensive AND, they may actually get small "dimples" in them from hail... it will show (in many not all) forms of metal roofs but that is NOT covered by insurance (cosmetic damage). 

One with 90+ members is great because it affords the HOA a lot of economies of scale with vendors thereby keeping HOA fees lower.Review the HOA financials and make sure they have a substantial reserve that would cover a hail storm deductible and/or other storm damage.Read the Bylaws to make sure they're rentable and check the pet limitations.Check the common grounds for any big ticket items that may need replaced soon.

Your biggest insurance concern would likely be hail and the possibility of totaling your roof.

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