Just mark your calendar of important renewal dates.

If you know something is going to have a long lead time (fireplace inspection, furnace inspection, etc...) then put it on your annual calendar to get those scheduled several weeks or a month in advance of when you need it.

Adding on to @Mihir Bhimaraju's comment, here is the calendar for CIREIA.

Once you pass the calendar year of the withdrawal - the train is gone.

From what I have been told there are two feasible ways to do this: Option 1: Sell Property #1 and within 45 calendar days, sell Property #2.

So my question is, is HA/VRBO keeping your calendar full and making you money?

If we are to manage a short term rental ourselves, we'll be driving down there nearly every week to prep it for the next set of guests if the calendar is completely full. 

crossing the calendar year to recognize the gain in - 2018 = as good as it's going to get for you.  

They mostly look at the photos, which need to be top quality.I would look at current rental listings in your area on Airbnb and on HomeAway/VRBO and look at their nightly rates and look at their calendars. 

I’m new so I don’t have any to contribute that are specific to REI, but from my other businesses.Waze + a calendar connection - easiest way to get traffic notices for departure time for your next meeting Outlook - it’s more powerful than the default iOS mail when it comes to signatures, scheduling, and managing emails Evernote - great note taking and overall brainstorming tool Dropbox - self-explanatory.