Your plan may cover all of the strategies you touched on, but over a longer period of time with definite transition points. 

What is the typical sequence of events to making a smooth transaction for tenant and us?

They are very often ready to downsize or transition to assistance.

Other unexpected repairs could add to that.On the other hand, everything may be smooth sailing and you’ll have 17k of reserves in a year and growing.I would suggest you do some contingency planning.

This is a group who are likely to be ready to downsize or transition into assistance.

Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.

The best mileage tracking app I ever used shut down but could be highly integrated with Evernote but did not require Evernote.Selecting on the maps from the app provides minimal capability.Overall I am happy with the product but disappointed with their transition to paid service.  

We started in Phoenix and are transitioning out due to pricing.  

One to consider would be Seniors with 20+ year ownership and low Financial Stability Scores (FSS)This group are often ready to downsize or transition to assistance.

Get a secure credit card (a credit card that is opened with a cash deposit) and utilize it until your score rises to a place where you can transition out of it...or keep it :) I'm 90k in student loan debt and my credit score is about a 740.