@Taylor Cook how much of the process have you automated?

Use good automation - a PMS, and a good pricing software.

Next, we tried RESimply, which was robust but not very user-friendly, especially in terms of automation.

UPS Worldport in Louisville is the largest automated package handling facility in the world, acting as a global logistics hub and supporting thousands of jobs.

Even for 1 property, I would use a PMS like Hospitable to automate as much of the process as you can.

Get an STR property management system like Hospitable to help automate a lot of things.

I have been looking at CRM's like Hubspot and Odoo and I tend to get a little overwhelmed because their tutorials all seemed to be geared towards those that have multiple people working on the CRM and all of this automation when all I want is a simple database.

You give them a spending limit and everything else is mostly automated it seems, but I haven't done it so can't say from experience. 

I recommend installing automation as one differentiator fromother properties.The furnishings must be durable and attractive to tenants.Quality photos and a property-specific website that provides extensivedetail about the property, the area, fun things to do, etc.Flexible lease terms.

How can I better automate my lease agreement being sent out, information filled in, and then easily signed by the guest?