- Know the property numbers: I would recommend AirDNA (paid version) + enemy method to factor income then back out all expenses properly- Know yourself: Why do you want an STR? 

@Chris Mason Thank you for the facts about the VA loan and the insights my friend, I do plan on doing a version of your example, unfortunately I don't believe the spread will be as lucrative in small town WI lol.

That is the real cliff notes version of the process. 

We would like to grow our portfolio as time, finance, and opportunity allow.Lastly, our oldest is headed to UConn for her PhD (6 years) and instead of paying to rent, our thoughts are to do a version of a house hack with buying a house/condo with her living there and then renting out one to two rooms to offset the costs of her rent.

If we assumed a modest 2% annual rent increase on the base $1,200/month rent it's at now, the 1BR version of this unit would bring in a total gross rent of $157,675 over the next 10 years. 

I think it may be a cut-down version of QB, but I don't know for sure.

The QBO class tracking feature, found in the more expensive Plus and Advanced versions, is used by many investors.

The Mac version is not as robust for Real Estate as the Windows from what I hear.

Tell them to buy a portable version?

As long-time QuickBooks Desktop users, we were working with the 2019 version.