Start to evaluate deals based on the income approach and you'll do much better long term investing. 

On insurance side of things, there is a lot of variables.

I think I've talked to maybe 2 tenants on the phone so far, and I didn't mind because there's a lot of scams online.

I've separated out electricity but not water (never heard of sewer being separated) and I've always had separate gas meters on my properties but have separated the heating system on one.

I saw Macon in your subject line and just assumed Georgia!

Software is a common question on BiggerPockets.

I've also leveraged that capability to build some pretty cool dashboard on my end to occupancy, revenue, and cancellation rates across all platforms. 

Each should be able to operate on its own.

Like should I have a folder on my laptop for the tenant and keep a copy of each payment I receive from them?

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.