There are people who have an entire business helping you set up and design a STR relatively quickly (3-7 days) depending on size of home and complexity but you are going to be paying a bit of a premium but you do save on the headache.

It will pay off. 

He will pay sales commission but get his BHA back and have lived for rent free. 

Your first year will be a learning experience, you will want to be close to the action, as you may not have the capital to pay someone to handle everything.

what would be the justification for paying that much?

I pay $875 (including principal, interest, taxes, and insurance) and rent it out for $1,625.

I'm thinking if I ask the tenant to pay the other half, I'll probably need to make an amendment to the lease to reflect that.

I used $80k to pay off personal debts and $50k to remodel it by myself with my two hands.

The garage and the fact that a long term tenant was in place paying market rent.

This is a the perfect vehicle to use for short term like buying a  property with cash, then refinancing the property to pay the line of credit back in full, and use it again.