If you move your primary residence, he will lose yous tax advantage on the investment property. 

Some sellers may not care and those that are in protected class's IE non english or simply not educated might still get taken advantage of..

Quote from @Christanne Wright: Working with STR owners has taught me that you need to have a discussion with a Tax Strategist or your CPA to see if there are any opportunities that you can take advantage of.

You have some unique advantageous Tyler.

The choice depends on their priorities simplicity now or long-term tax advantages.

@Sheena Varghese@Basit Siddiqi is spot on with the two categories. 

It seems like a lot of short term rentals don't get updated and that's a key differentiator that we're hoping to take advantage of.

I spent close to six months looking at various vendors in the space, and below are some of the ones we ended up choosing (including one of our favorites, Hospitable).Each of the hours underneath the categories refer to what I estimate the monthly time-savings are by deploying the technology within the box for us.

Active investing takes your time and some type of knowledge or skill that gives you an advantage over other investors.  

One way or the other may be more advantageous to you.