Our STR/MTR portfolio typically sees around 80% occupancy, and I’ve noticed that the online travel booking sites often push properties with consistently great guest experiences.

That sort of thing is typically negotiable.

typically no special license is needed when doing it for hard money loans that I am aware of. there may be states like california and nevada that are tricky where lenders need a license of some sort but for most part brokers i have seen are not licensed. 14 or 15 states require state license and NMLS registration.

Consult you insurance broker for specifics but I found this policy to be very protective and reasonably priced.With regards to an umbrella policy they are typically good to have.  

• How do leases typically handle furniture/appliance damage or wear?

What you will find is they typically appraise for far less than the hands off cost to add the ADU.  

You should be able to pay off the loan anytime during that period, without any sort of penalty.

@Brice Alef-Torrisi putting each property in its own LLC is usually overkill.Getting a bank account for each LLC is typically something you need to do to avoid "piercing of the LLC corporate veil" (actually depends on tax selection you made for LLC), but is also overkill.You haven't indicated how you are holding the deed for the latest property.If in your name or same LLC, you don't need a separate bank account.If in separate LLC, you can create a Master LLC, have each property LLC hire the Master LLC to manage their affairs, and just get a bank account for Master LLC.This is an opinion, not advice, so lookup CPA Frank Alcini in Troy for expert advice.

Has anyone run into problems with this sort of lending?

Passport 2. 2 Months Bank Statements showing downpayment + closing costs and reserves (typically 12 months) 3.