Creating direct booking site for STR's. What is your experience and advice?

[Jacob Switzer]

We are creating a direct booking site for our short and medium term rentals and I am interested in hear your experience and advice. 

We use Hospitable.com as our PMS and they make calendar integration and payment through stripe easy enough. 

I am wondering how people handle security deposits (or other protection) for short term guests?

How do you handle leases for medium term guests, 1-6 months. 

What marketing do you do?

What other advice can you give?