We planned on using this as a STR and were expecting 50% occupancy.  

I was thinking starting with that to growth some financial aid. 

Did you tell the owners that you plan to not occupy the place?

However, I have an actionable plan set into place now, with the monetary means to set my plan into action.

In my experience, short term rental managers charge the most, followed by room by room, followed by longer term management.There may be an opportunity for you to do this yourself if you plan to continue living in the home.

Right now the stock market is in a short term decline and not sure what investments you currently hold in the 401K and how to time the market would be a better question for an FA (Financial Advisor).

I plan to purchase a 2-unit+ property as a first-time owner to get all the advantages Maryland offers, and scale from there. 

I think HH provides these new home buyers the opportunity to purchase a home with some financial flexibility being able to rent out portions for extra income. 

I work for Global Realty Group LLC in Cibolo, we require it for our landlords and also like to be added to the tenants coverage plans as well.

Planning to put more then 20% Downpayment .