There are companies/agents that specialize in what you are looking for.  

We have a property manager in Colorado and another one in Ohio that give us pretty good annual reports.

I just recently found out that my company is closing mid summer.

First, I'd try to find why the water is doing that as you can replace the siding, but if the water is going to keep doing it, you will have that problem again.If it is isn't a condo, I'd talk to your insurance company.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

You can assign classes to each of your properties to break them out separately on on your reports. 

I'd like some reviews on property management companies in these cities as that will be a big deciding factor for me since I will be an out of state investor and this will be my first investment!

We can help you out with offmarket aquisition and Property Management in Cincinnati , give me a call to see if we have answers to all the woes you had with your previous PM companies you used , or if you are new to investing in cincinnati we can start from basics and help you put as well 

Is it to our advantage to mention that we're just a regular couple, not a company?

If the new owner gets title insurance, the title company will usually discover the tax sale and redeem at closing.