This might be hard to get so I’m trying to weigh the benefits of doing this.

@Rena Spooner, in general terms, buying a second home a the top of the market will lower the benefit (in coming years) of having initially bought at the bottom of the market. 

Use keyword rich content when crafting your descriptions.Check out what other people are renting their places out for on Airbnb and compare it to yours and adjust pricing accordingly.

I know as my business grows, I would gain more benefits and be more productive,as Brent suggested.

Can I still benefit with using the house as a primary residence?

The main benefit of short sale houses is they are in a good condition due to the homeowner still lives there.

But the benefit of the increased risk may be that t keeps away other more risk averse investors.

Doctors used to buy old apple farms for this reason.Most of the tax shelter benefits went away.But at his age, he might not be looking for more income.

You may want to look into getting real estate license soon however for the benefits of MLS.

In order to get the cooperation from the owner you will very likely be asked to make an offer-do so subject to financials and inspection you can always adjust the numbers depending on what you discover.