Again, Especially if they’re using a PM and get a pretty little report of all the income/expenses and a 1099.

However, it is likely that I will want to use my commissions to fund repairs, use as a down payment, or even cover expenses on these investment properties.

We may be buying and completely gutted house soon and hope the things I want inspected (basement walls bowing, sewer pipes, and basement floor) don’t turn out to be too expensive to fix everything should turn out pretty good for that property as long as comps support it.

You are better off budgeting money for maintenance and capital expenses and keeping a reserve in case issues arise faster than your budgeted money gets socked away from incoming rents.

I noticed with Airbnb's dynamic pricing it is a lot lower than what my pricing software/revenue manager recommend. 

I've had people get lower rates at no cost than they were offered by another lender WITH points. 

I have 5 LTRs: 3 lower-end units and 2 top level luxury units.

Then, run your numbers on the potential STR income - what are your expenses going to be (they will be more), and what is your projected income based on looking at competition in your area on the sites?

I intend to purchase an owner-occupied multi-family property this summer and would like to take advantage of the lower 5% down-payment.Question: What, if any, are the advantages of one of these scenarios over the other?

You can lower your risk by putting more than, say 30%-40% rather than putting down 5-20% down.Using new builds or turnkeys as rentals would be a good way to get started and lower the risk for cap ex, so this could make sense.