3 separate recent studies show it is currently cheaper to rent than own in virtually every large market and that it has never been more so than currently.  

You don’t have a large enough portfolio of houses for a lender to feel comfortable without a personal guarantee. 

Yes, that makes perfect sense, especially in such a large transaction to find the replacement property.

I read an article somewhere that Airbnb was going to negotiate with large Apartment complexes to allow the tenants to do short term rentals.

That is a complex question to answer since both states are large and depending on where you live, quite varied. 

It's just what does that really mean.I was a part of a team that managed a big brand for a large tech company.

You said, why, not what.Because there is going to be a large drop in licensees.

Give large discount for a medium term tenant and max out on the busy season with short term.   

Consider looking for a large single-family home with the ability to add more rooms or bathrooms, then rent it out by the room. 

If an employee calls out sick or quits unexpectedly, you will have to step in to handle the day to day of your business.The amount of work required from you as the owner will depend largely on what services your mat offers.