Justin,Look at Homeaway and Airbnb for similar properties, then see what their rates are and see how full their calendars are.This should give you an idea of how much they are bringing in annually.If you put it this in a spreadsheet and make a column for each property it should be easy to do the math.Then you'll need to deduct for Mortgage payments, cleaning, utilities, upkeep, advertising and Property Management.You can pretty quickly see what the numbers shake out to be.You could also play with the numbers like different mortgage payments, PM or doing this yourself, different rent levels etc.You may be happy with a 50% or 75%  offset on your overall costs since you primarily want a second home/vacation place for your family.

They would just need to all be able to sync calendars between each other.

Send me a PM and we can get something on the calendar!

When I started my Airbnb, I filtered out all the like item places I would be competing with. then I looked at their prices and calendars to get an idea of what kind of business they  are doing.

Homeaway keeps my calendar full Airbnb does not, it is as simple as that for me.

It integrates with google calendar well too and I use it as a project management tool to keep track of my tasks.Web based with an app.If you're in you first year of practice, they also offer 6 months free membership, otherwise it's 5 weeks.Pat

Customer Support said the year of the disc must match the calendar year!  

The last thing I will add is I think it's worth factoring in that from Charlotte (or Apex in your case), the feasibility of using the property during some of the open calendar dates has a value, and should be taken into consideration. 

Have you educated yourself on the process, on what it takes to choose a market, to stage, to set up the profiles, to manage the calendars, to automate the guest messaging?

Look at his calendars very few bookings for November and beyond.