I have seen studies that show that when the utilities are paid by the tenants themselves directly, that the costs are reduced by 20%. 

If you’re in a hurry to find a deal fast then you might be going at it with too much desperation that a seller can feel and get nervous about.P.S I am a direct buyer or not a Whole Seller.

And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

The more mature platforms that are designed for landlords/property managers include Rentec Direct, Buildium, Appfolio, and Rent Manager.

When maintenance is scheduled, we send out a reminder, and if they won't be home, they can easily authorize entry.Sometimes, our contractors will contact tenants directly to arrange the most convenient dates and times for visits.

But as of the last 6 or so months I seem to be losing direction.

It's designed to protect assets in the event of lawsuits, negligence, etc. and it only applies when there is underlying insurance coverage. 

Should I find a few buyers before I go out trying to find sellers, or should I start with sellers, then look for sellers directly or bring it to other wholesalers?

I feel direct mail is another great method.

You can acquire that debt across the direct property and / or the DST/TIC.