The direction may change as you learn and make connections but without the map it's easy to get lost. 

Be aware there may be changes coming up to the taxation of primary residence sales, make sure to talk to a CPA specializing in real estate when you sell your home.

At what point is it legal for me to change the locks and start cleaning the place up so I can start to recoup my losses.

By midnight on day 45 you must have a list in place and from that point it cannot be changed and you must close on one or more of those properties.You do not have to be under contract in that 45 day period but it's a really good idea to mitigate risk. 

However, in my opinion that is much more of a business than a passive investment because there is a lot more day to day involvement (i.e. cleaning, advertising, changing rental rates based on day of the week/time of year).

I think we were lucking to sell as fast as we did.

Fast forward three years and soon leaving university for the real world, I am now considering refinancing the loan (17 --) 30 years) on both properties in order to buy a third and/or fourth property.  

Something has to change or this will continue.

If he doesn't find something that changes everything I will have a conversation telling her I will allow her out of the lease and that she can start looking for a place.

These events are exciting, engrossing, and have been life changing for many people.