How safe/what grade would you assign to Academy, Kingsway West, and the surrounding neighborhoods?

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.

I used to use Corel Logic and Land Safe but it appears they know longer are in the business.  

Hi, Jacob - to create a lease I recommend you use an online service like Avail.co or Rocket Lawyer to draft a state-specific lease.

Do you really want to play it safe your entire life?

Best of all, online abilities is good and I can see everything on the note.

Does that seem safe/conservative enough?

Even if you have good folks on the ground to help you out, you are going to be making trips to take care of things that those people are unlikely to do, not the least of which is risk management:  Making sure your property is safe for guests, inside and out.  

So I do my networking online.

This is a general response.According to NAR, 98% of people see a house on-line before they even contact an agent.