So, if you are a licensed Property Manager and your Management Agreement specifies this role, it should be fine :) 

Personal finance does play a huge role in real estate and financing if you are going with a traditional loan from a bank but the amazing thing about real estate is there are so many low risk options and ways to gain property.

I am torn on weather to stay in my role and grow a portfolio as fast as possible or take a good opportunity in a sales role and have a higher income to grow that portfolio.

I currently work for a healthcare IT company in an analyst role and have been working from home in that capacity for just over 2 years now.

For your academic exercise to work, there are two variables you must hold constant. 1.

Just be aware of the inherent conflict of interest there and know that their role is to get the best price and terms for the seller, and not you. 

You could set option purchase price based on appraisal at the time the option is exercised, I’ve seen this done.  

Do a gross rent multiplier exercise/comparison?

That's just a hunting exercise to keep going until you find a few that will do it. 

I would definitely still have some sort of operating/partnership agreement up front, where roles and responsibilities are clearly defined. i would also include exit strategies. you do want to be careful about being in business with family. having everything laid out up front can help.