I've trained people at my jobs when I was a senior accountant to controller.I've used Yardi Enterprise (old desktop client software)Yardi Voyager 6s & 7sYardi Genesis2Reason why I say you won't be able to find a tutor is because no one is going to spend $15K a year to use as a training platform to mentor and tutor people.

On average, you will spend 10% of your income on maintenance per year.

They should not be charging a fee when the unit is empty; so the percentage vs flat fee argument has little substance in this aspect. 

I am not sure what the availability of cleaners in that area so I would spend time right now see what is there before committing to a property.Also, if you are spending 2k a year on fixing or replacing stuff, you are getting the wrong guests.

You can spend as little as $100 to form an LLC, or you could use an attorney and spend $1,000 or more.

There are a lot of inconsistent contractors, so really spend some time vetting them. 

Spending a ton on property management doesn't seem like the best move.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

The truth is that you have to SPEND 20K to go to their school and learn the ropes.