Would the closing attorney or lender take issue with me essentially selling to myself, therefore no real money exchange?

Mortgage payment is $1,000 on each house, so you're essentially earning $500 per house or $2,000 a month.

If I own a property, I can essentially use it as a savings account...

They essential strip the offending party of their license as apart of this process.

You not only consider the number but it is essential that you consider the % of their credit limit they have available.

Then pick  your best quote.Chances are almost all lenders are going to quote you essentially the same rate and/or will factor in discount points or lender credits to raise or lower the rate. 

If you can do this, then it is essentially the same scenario as selling your home and buying a multifamily unit.

The majority of buyers are looking in specific areas, due to school districts, neighborhood safety, accessibility etc.3.

For instance, our property management company only covers small portions based on the safety of the neighborhoods and its proximity to our investment properties.  

The method that I have been experimenting with at the moment is essentially taking a pre screening Google Form that I got from someone on Biggerpockets a while ago that I have been sending to everyone that reaches out as the first step before they come in to see it.