I think I will not let him make this upgrade as a 5 year payoff would require over $100/month additional rent.  

To maximize the number of transactions you’re involved in you will need to:Be Top of Mind when they think about moving - which requires consistent reminders.Be seen as an Expert – which requires a consistent message and Evidence of Success storiesGain their Trust – which requires communicating integritySo, start out by listing everyone you know in an Excel spreadsheet.

A DSCR loan is going to require more down, have high fees at closing, a higher interest rate, a pre-payment penalty, and will require you to have cash reserves that you likely don't have at the moment.

The biggest thing with 5+ units is everything is more expensive, and the inspection requirements (depending on the municipality) are often more rigorous.

So, coming up with more capital to invest in another property requires some creative thinking.

If you ask the manager to justify a fee and he starts hemming and hawing, move on or require them to remove the fee.

I also do not stop marketing unit including open houses until i have a holding deposit.  

The lease should have a provision that requires the T to comply with HOA rules.

A BRRRR could maximize returns by recycling capital, but it requires solid execution.

Do you require renters insurance?