Am a single parent with two kids, one of whom is about to enter college; can't afford to make a silly mistake.  

I've been holding onto my W-2 income simply for the allowance of getting a home loan and realize once I convert full time 1099 my chances of getting the loan decrease significantly.

I want a property management team to start off with, simply because I don't know the ins and outs, and need people who make this their business.

You will simply have to just add these costs into your analysis to see if it is worth it.

As a small time RE investor (two properties), I'm thinking it just makes the most sense to 'shift' some of the deductions I used to enter on a Sched A over to the Sched E because of the new rules/deductions with the Tax Cut & Jobs Act.

With $300k of student debt hanging over your head simply qualifying to buy additional investment properties will be extremely difficult cause your debt ratios will be totally blown out. 

My time is simply more valuable being used in my profession.

Your book will still be a mess.You get a typical bookkeeper that can pay bills and enter receipts.

There are myriad reasons why the rates are lower for a primary residence vs an investment property, but simply put, if the mess hits the fan, what property are you going to let go first, the one you're living in or the one that you rent? 

To simply buy an above average cap rate means you have to buy an asset at below market value.