Multiple Phone Numbers for Multiple Markets Vs. an 800 Number

[Luke Carl]

So I've got a property management company that only manages properties I own.

I'm currently in 4 different markets. 

I've outgrown Google Voice (They took my phone number away forever at 2:00am) so I'm moving to Grasshopper which I would have done months ago had I known it existed. 

I'm trying to decide between one 800 number (that is textable) or getting a different number for each market. I see benefits to each. 

Pros of Separate Numbers

It's a lot easier to get things done with a local number. Housekeepers/contractors/plumbers... They see a non-local number and they roll their eyes. 

Able to keep things straight. This number is this group of properties. That number is that group of homes.  

Cons: 

Toggling between numbers on Grasshopper app. 

Possibly creating too much work for no reason

$10 per month for each extra number (not an issue if the system works) 

NOTE: Some of these are Vacation Rentals that legally have to have a phone number with 24/7 access. 

NOTE: I'm not answering these numbers. Employees, specifically my VA will have full access to the phone number(s) Although I will have the option.

Your thoughts on which system will work better? 

Thanks!