To be honest, they don't always start out as great deals, but when you buy in higher quality areas, they get better and better every year. 5-7% annual rent growth and appreciation adds up to a significant amount after 5 years or so. 

What would be the very best episode to start her out with?

Use that income to start a business that will create more income for you.

I started my STR with my Pool as is and this year added a Pool Heater (unfortunately the pool is only operational during the summer months).The only other thing to consider and it really depends on the condition of the pool, you could possibly delay on restoring it for now.

My advise is to start with single family or a small multi-family ground up project first but this market environment is truthfully not the time to be completing any ground up projects unless you are self performing the construction which it doesn't appear you are in a position to do.There was a recent Philadelphia  forum chain started by someone else who was contemplating ground up in a similar fashion to what you are proposing and I cautioned they would be better off buying something that was newly built and believe after conducting their own diligence realized it was too cost prohibitive at this time to build with 3rd party GC's in Philadelphia when also accounting for the interest rate environment and cost to build.

To facilitate an informed decision regarding my suitability for the role, I would like to propose starting with a trial period which would allow you to evaluate my performance and see firsthand how effectively I manage properties remotely.Thank You.

I am looking to take that step and start to gain experience. 

I am also concerned that when the economy starts to weaken, the more rural areas will get even more challenging.  

Not sure if my response is still relevant - I've also started receiving mail promos from attorneys.

My end goal is to start investing myself.