@Caleb Rehg  I would advise your first step is to search this site for college student rentals and student rentals and read all you can. 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

But it is very risky and you can lose all of your properties if things go wrong.

The program stipulates that you MUST stay in the home 5 years or you lose a pro rated portion of that 8k.

For anyone that is looking at developing or purchasing an STR in Packwood, WA I would take a peek at the numbers that are on the rental sites and the amount of bookings. 

But for some, including myself when we bought in 2015, breaking even or even losing a little each month was okay in order to own a property in Hawaii that we could also use ourselves.- Does the condo have an existing STVR permit or will you need to apply for it?

It's like investors who hire property managers and don't manage them - they lose money.

That’s assuming you don’t lose money to vacancy, capex, etc etc.

If you build a buyer's list and you send them deals where the repair costs aren't close, you will lose them.

There are other sites.