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. 

I may go through a title company that has a lawyer on staff that said he can draft something up.

This is a very overwhelming journey to be on and I'm just hoping that I have enough knowledge to get started and not get crushed on my first deal.

Meanwhile most property owners have no clue that property managers like Michael and their staff and sub contractors are performing services on their property without appropraite insurance but want the wyoming LLC, florida land trust and separate "management" LLC to collect their rent. 

Just in the research stage and processing all this information has been overwhelming ( In a GOOD way) I already know, San Diego is not the place I want to purchase, so I'm looking into Midwest areas, close to other family members.

You have to manage them, but they are now your "Staff" to take the stress off your shoulders.Is $30k a lot per year? 

The combination of rotting food, rat droppings, and general decay was overwhelming.

The good advice here is overwhelming and I appreciate all the different perspectives.

It's a thrilling and rewarding world, but it can also be overwhelming for newcomers.

Otherwise it's going to be super overwhelming trying to understand a half dozen markets.Once you determine what city you'll be investing in you can start drilling down.