I am a new investor but wanting to fully understand every aspect of being a landlord and analyzing properties. 

Sure, there is value in all aspects of MFH but buying an existing property will provide you with immediate income but only when bought right. 

What about other aspects such as desirability from location on the street, how appealing the entrance or display window is, restaurant vs office space, etc?

There are certainly some advantages to short-term rentals but just keep all aspects in mind.  

What would be your analysis of each of the investment categories I mentioned.I had used High Yield or Leverage as an example you can assume any riskier asset class publicly traded in the stock market. what I am seeking is a way to assess say the risk involved in investing in a specified category versus another and the commensurate return (reward) I should expect keeping non-financial aspects out of the decision.So again, for example, hypothetically I invest this 30k in a Public REIT I should expect maybe a 5% (assumed with no basis) return YOY or I buy a High Yield ETF that returns 11% (again assumed with no basis) versus if I leverage this to buy a residential property then how to asses this on the same risk-reward spectrum and compare the two?

For example, if you did 100 hours of carpentry work on your flip and you found out that a carpenter makes on average of $25/hour in your area, then your salary for that aspect would be $2500. 

I have grown up working in a national contracting business, and am therefore familiar with how contractors work and communicate (I really enjoy this aspect of RE).

The human aspect would be to help her. 

I'm diving head first into the learning aspect as we speak.

I own 30 units and I personally feel like I want to stop acquiring more properties and grow in other aspects of Real Estate