@Arthur Savery, This can be a great game plan called a diversification exchange. 

I currently have a homeowners plan with Allstate and plan on asking them if they have something like a short term rental rider plan that I can add in addition to my current plan.

Johnson county is expensive, nicer suburb.

I am planning on leaving the brokerage to go somewhere that is more investor friendly, and somewhere with a broker who knows what wholesaling is.

I just acquired one from a PM where they were charging a tenant a resident benefit package and a building protection plan.  

College rentals are relatively expensive and come with their own unique challenges:1) Roommates not getting along2) No one cleaning or maintaining the property3) Weekend party damages4) Etc...While you are considering what to invest in, recommend you also figure out the property Class you want to invest in.Why is Property Class so important for investors to understand and apply in their investing strategies?

Maybe not the easiest deal but with the best upside.Philly needs jobs, attracting tech jobs should be a plan.

I am in the process of studying for my licensing exam in the state of Tennessee and plan to work in the Chattanooga area upon completion of the test (which will be quite soon).

At every single point in history, people think that the market as it is then, is so hard, and so expensive to get into.

Do you have an idea of what your time horizon is for your investment plan?