For smaller items like this, I might use @John Underwood 's simple method: For bigger items or if things start being left and requested back more frequently, I may indeed need to both charge for shipping and maybe loop the person who cleans in on it ~ She'd likely appreciate a bit of extra, relatively simple work.

I would look at ways to add value (extra units, bedroom count, etc.) to maximize the house hack.

There is extra inspections involved.

-Booking.com is a very large and established company that has been around much longer than airbnb and vrboCons:-more listings to make sure are all staying maintained assuming you are also on airbnb and vrbo-you have to pay them their commission back at the end of each month which is a pain in the a** and is an unnecessary extra step-payouts can take longer as you mentioned-it has been impossible for me to find anyway to contact customer service over the phone and instead you have to refer to their forums and FAQs for any answers you need.Hope you found this helpful.

The home has a separate studio in the back for rental income with solid rental history but I am still trying to get a sense of the likelihood of consistency in renting it out as a short term or mid term rental. 

If the buyer is serious, two extra weeks won’t be a big deal.

I am going to add a bit more context, please provide any extra thoughts or insights. 

With careful planning and consistent effort, you can create a portfolio that aligns with your long-term goals.Good luck!

@Chani Walker These fees are consistent with the industry norm.

They did have an extra step to make sure that you were the owner of the property, but otherwise it was not bad at all.