I saw your other post and it appears you're asking pros on this forum specifics as it relates to your return for DIY preparation purposes. 

We frequently provide value to the forum by answering questions and posting updates to the tax laws they relate to real estate.

This allows me to travel for almost free internationally every 15 months (airfare wise).I don't go out and get drinks (I'm 23 so this is not very typical) unless it's professional related and even then I do it sparingly. 

When we were smaller, we setup a relational database and email parsers from each booking channel, and used that to unify the reporting.

If the guy is a registered sex offender, go to the police ASAP and ask if he's registered for your address.

@David Waddleton yeah, I can relate to the spot this puts you in.

Being my age I am considering looking into another job that relates to real estate that will give me more experience and insight into the industry which will allow me to apply it to my own future portfolio even if it means taking a reasonable pay cut.

There are a wide spectrum of companies that would fit that description.Most local residential real estate investor companies are relatively small (in terms of the number of employees, not assets or profits) and they aren't going to care very much about which specific area you majored in.

@Alex TurchettaOn a slightly different but related topic - you cannot really save taxes via S-corp if you're a contracting psychologist.

I understand that 50% for expenses is a very rough number and will vary depending on the property but it seemed to be a relatively conservative approach to start with until I come to know my market better.