Have you had the “sight unseen” tenants wanting to break leases more frequently than tenants who were able to see the unit and the neighborhood first hand?

You can see the obvious upsides for me here: I'd get my property; I'd spread out a lot of the risk; I'd keep a pretty big upside on the deal; and I'd end up with a lot of cash. 

After we got in and were able to see the roof, it looks like it's about 15 years old and has a couple layers of shingles installed.

If you are looking at zillow for comps I would suggest you look at actual MLS comps instead for 1624 square foot 5 bedroom 2 bath homes to see the real after repair value on this property.

Where I see the greatest opportunity is all the uneducated investors mortgaging their primary residences and taking personal loans to buy rental property and have zero reserves.

I see the rates but it seems hard to see investment numbers versus numbers if you occupied. 

You get to see the process, be around real estate and learn how transactions close. 

I'd like to see the economy stabilize a bit, in order to get a better idea of what the future holds.

We've found it hard to get the potential tenant to fill out an application before they see the property but if you can do it that way then more power to you!

As for timing, I really don't see the benefit of waiting unless her actively managed funds are vastly outperforming the great index.