I was thinking for my first property at targeting the area in MWC close to TAFB, Rose State College.

Instead of a pool table, I would put a horse shoe pit outside along with a grill. 

Rose, I get why you're asking, but it really is different on a case by case basis!

Fast-forward 1 year and I am in your shoes! 

On one hand it's enticing to spread the capital among multiple properties to diversify and kick start my portfolio but on the other hand I know eventually I'm going to want to scale into larger properties for maximum cash flow.What would you do if you were in my shoes?

Changing your mind after 6 months would surely question your intent.If I were in your shoes I would talk to Tim about your options for purchasing a second property outright. 

I have a potential Class A property near San Jose's Rose Garden Neighborhood.

I have a potential Class A property near San Jose's Rose Garden Neighborhood.

I am not a lawyer but my personal opinion is that LLCs are over-sold to beginning investors.Put yourself in an ambulance-chaser's shoes.  

While AirBNB is certainly imperfect about how they handle resolutions, I think there are some valuable insights here about the necessity of documentation.Putting myself in AirBNB's shoes, photos and invoices are absolutely critical to resolving disputes and damage/expense claims - otherwise, they would be at the mercy of people who wanted to abuse the system and make frivolous or false claims.