I know how to use the basic features of QBO, as I do my own expense tracking, but my Bookkeeper is needed for the more complex entries (Loans, capital balances, reconciliation, data entry from PM monthly statements.)I spend almost 8k per year in QBO and Bookkeeping costs (Not including my accountant or tax prep.)

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

They have median household incomes of 52k and 55k respectively.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

Under this rule, if you spend at least 100 hours on the property and no one else exceeds your time spent, you can qualify as materially participating.

The number one mistake that I saw buyers making was jumping right into negotiating (and not very good negotiating at that) without first spending the time to build rapport.

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.

I currently work with investors looking to build their portfolio with single-family, long-term rentals while managing for them on the back end, making is hands-free for the investor to still work their W-2 job and live their everyday lives and spend it with family, hobbies, etc. 

You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

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