I think that strategy certainly engages a point of empathy on your renters and empathy is a necessity in winning a negotiation.

That’s a necessity How much do you need to live on in a year?

Because it was a necessity of something fast we went with Obie Insurance and had not problems getting hooked up with them.  

However much I'd like to get out from under the necessity of lawyering, I make a pretty good hourly rate and probably would be able to make more by billing legal fees and hiring a management company to handle the apartment than cutting my lawyering hours in half to put more focus on the RE biz.Maybe investing in smaller multi-family would be a good compromise.Any advice and recommendations would be greatly appreciated.

IF you are willing and able to invest the years of time, effort, and money and IF you are able to perfect your systems and get a good team in place, then at that point it can be profitable and passive, but understand that those are a LOT of IFs ... you need to go in with eyes wide open to this fact, and not expecting it to be like buying a stock or a bond ... and no, buying turnkey does not excuse you from the necessity to do this, because the turnkey company's systems are optimized to maximize THEIR profit, and not necessarily YOURS.

Again, it's a hugely powerful tool, but not always a necessity.

My first rental property was something decided out of necessity and not as an investing decision, so I was looking for any advice for estimating expenses. 

The sole 'negative' might be the lower returns due to the necessity of the Property Manager, which is required for you only because you are not local to takeover yourself. 

First, out of necessity to save money, and later on just because I felt like I had learned over the years enough to do my own contracts.

Obviously he will be a necessity for my 2018 tax return.