check out airbnb or vrbo for what rentals go for in that hood and look at the calendars to see how often they are rented 

Look at the calendars of several similar properties.

But I'm putting the next one on the calendar.

Mortgage insurance is calculated annually, using the outstanding balance and LTV ratio.So, while your payment will be the same for the entire 12 month period, it will change for the next 12 month period based on the reduced principal that is outstanding.Keep in mind, the annual calculation is completed upon the 12th month of the anniversary of the loan origination, not a calendar year.Here is an example from my own portfolio for an FHA loan that my husband and I obtained while doing a house hack in 2012, that has since been converted to a rental property....Original loan amount $247,926Year 1 PMI - $251.68Year 2 PMI - $246.94Year 3 PMI - $242.01Year 4 PMI - $236.90Year 5 PMI - $231.58Year 6 PMI - $226.07We are currently in year 7. 

Post pics ASAP but, unless you've got a self-imposed deadline that you'll move heaven and earth to meet (which is what I did), give yourself plenty of time before you open your calendar for reservations.  

The calendars are synced, but that's the only thing we really have that is automated.

If your tenants have not been there a full year yet, you can just give them 30 days notice (unless your lease says otherwise).And, in CA, notice is calendar days. 

In CA, you have to hold the tenants items for 15 calendar days after they have been evicted. 

In Florida it may be usual to just have them rent for the calendar year, many areas function on that model. 

Meanwhile, his tenant has reminders every 6 months on her calendar to ask AJ if there is a status update.