And the replacement property must also be purchased with the intent of holding for productive use.Most folks feel comfortable with anything more than a year but there could always be situations where a hold period of less than (or more than) a year are needed to demonstrate your intent.On the plus side for you would be1. it appears you frequently hold property (the 2010 purchase) for longer term.  2.

@Lane OttoI’m thinking AirBnB would be the best way, if she’s comfortable with it.I know a couple empty nesters who have utilized that extra space for AirBnB income.

I talked to my CPA and he said that it wouldn't be advisable to have a lease agreement, but a living agreement of house rules he feels comfortable with. 

When I meet local buyers (which I'm doing ALL of the time at local REI meetups), I ask them what types of property they're looking for, where they want them, what condition they're comfortable with, and what price range. 

If that’s the case, decide how many units you are comfortable managing with your schedule and consider how you will meet any needs they may have (such as midnight property emergencies like heat going out, plumbing leaks, etc), and find some maintenance and repair people that you trust to handle the big things you cannot do yourself.

This home comes equipped with 3 Bed and 2 Bath, features a big open kitchen, dining, living, and even a family room.

The other option is also good however as young investors I would start where your comfortable, accomplish that and then consider expanding geographically. 

Never want to win so badly that you will forego your future by waiving things you are not comfortable with or experienced enough to waive.

Where's your comfort level, and do you have cash to put into marketing. 

You should only be flipping a house when you have watched someone do it and feel comfortable and confident that you know everything you need to so you don't lose money.