I would love to find a software to help automate the following tasks, there are lots of options, most at $40/month, would prefer cheaper but will probably pay this for the best software that can best handle:- creating a direct booking website from my Airbnb listing, I know some websites have an auto-builder which would be preferred- handling automated messaging- handling calendar and payments, including add-ons- sending agreements and collecting and returning depositsI am overwhelmed with the options and suffering analysis paralysis. 

One who has invested millions of their own money to build automated systems in place to the point where all you have to do is put in $50k per house and it doubles every 5 years.

You are missing out on an opportunity to train your inherited tenants to pay on time (and potentially extra revenue) by not using an online rental payment option where you can automate your late fee collections.

Especially an automated valuation from a website. 

He was very system/process/automation oriented, enthusiastic, and well experienced.

I use Hospitable to automate guest communication for my tenants, regardless of if they booked manually or via Airbnb.

Take a minute to familiarize yourself with the do not call list and rules about doing robo calls or using an automated dialer before doing any sort of telemarketing. 

IMPORTANT:--Guest communications, including setting up your automated messages--Price adjustments (key into seasonal pricing and important events in your area)--Listing description and noting amenities--Guest reviews--Learning from experienced hosts with great reviews (you can do this on many social media sites, including the Facebook group, Short Term Rental, Long Term Wealth)UNIMPORTANT:--Watching your Ring Doorbell camera--Obsessing about minute details that other hosts are freaking out about--Being a control freak about ANYTHING related to this business. 

Some work that comes to my mind is:1) Managing tenants to get rent paid2) Diagnosing a repair issue and getting the right team to make the fix3) Fielding messages from prospective tenants on advertised rentals4) This list goes on...I've found a company that automates rent collection and income/expense tracking for free, but I'd like to replace my property management portal altogether and feel I'm only half way there (certainly a tenant facing chat bot would close the gap).

Your conversion rate will still be 0.033% but at least it is automated.