I am adding about 20 more this year, but there's one small pocket I'm struggling with the financing on (honestly, due to Huntington Bank dragging their feet on items, etc.), so I'm seeing what other options there may be. 

Often times they come back with a list of repairs that they would like to see to protect the home or mitigate liability. 90% of the time those items were on our list to fix anyway, and sometimes we even haven't done before we get the letter from the insurance company.

I’m a 23 year old military member and upcoming veteran :) !

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There are state specific items to take into consideration.

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

Then at the court you will be the "prosecutor" and must out line the violations according to the lease, and show the efforts you gave your tenant to solve those items.3.  

There's other items such as this where it may be helpful to talk to a CPA/EA for a little tax planning, especially since you'll likely get caught up in the passive activity loss limitations if taking bonus on a single rental property as I often see.It's also useful to mention that even if you do the cost seg study (I'm assuming you're doing one to be talking about this), you'll still benefit from accelerated depreciation in the form of shorter useful lives on the assets where you received bonus from.

Wind is one of the subtle items that Insurance companies are starting to exclude. 

The itemized damage estimate that my insurance provided me lists an Actual Cash Value that is 15% higher than my Dwelling A Coverage.