STR you personally can enjoy the property too2.

I personally wouldn't charge for any of that if they left the unit in good shape. 

If you're asking for free advice from a stranger on the internet, I'd encourage you to find a different STR market unless you want to have a place in Kissimmee for personal use.

@Shiloh LundahlTheoretically assuming properties were identical in every sense yes because I don’t need cash flow and would rather have the extra $100k in equity.Now $600/mo could get you another $100k mortgage to get you another property that could potentially also cash flow but for me personally I am in equity play mode now income mode - just my personal choice but nothing wrong with the other scenario

Personally I feel he earned it that’s his money.

The cost of entry is low, and cash flow is high.You can find distressed off-market duplexes under 120k and SFH under 80k in B to C-class areas.

My worry with leaving the local agency is the personal attention that guests receive when they call.

This is a lender and personal question.Lenders look at your monthly Debt-to-Income Ratio.

Since the DADU is on the same property as my primary residence, can I place the DADU in an LLC, separate from my primary residence, to protect my personal assets from liability?

You don't get that from a random person you don't know well.