Personally I carry a liability policy for each property then have umbrella insurance for added protection.

Which leads me to a question of whether or not it is worth creating an LLC to begin with or having a Umbrella policy in place.

I want to sip umbrella drinks & be fed champagne & fruit from hot muscular men in loin cloths.

Other friends have seen the progress and want us to put their units under our umbrella now.  

Plenty of coverage in my opinion with a LL and umbrella policy.  

Your investments are worth a substantial amount of money and you are getting concerned about your personal liability - maybe its time for umbrella insurance or an LLC.

Since this will be the start of our real estate investing journey (opposed to our current residence) we wanted to know if we should look into a regular homeowners/flood insurance policy or an umbrella policy since we'll be acquiring additional rentals in the near future?

If your agent does not offer some sort of umbrella coverage, you probably have the wrong agent!

I've been around and evicted people and to eat 2 or 3 months is usually worst case senerio (considering you have good insurance and an umbrella policy for injury, or vandalism) this a month ago was unthinkable that this was even a possibility. 

I recommend getting an umbrella policy for $15/month.