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 believe, aside from house hacking, a LTR as your first investment is a great option since it will teach you many different aspects but not deal with the headaches of a STR. 

Look for other types of renters who aren't necessarily affiliated with hospitals or go just outside the neighborhoods immediately surrounding the hospitals and market it as a good option.

You may be able to find a value-add property there that gives you an equity option in the short term.

Think if there are other options. - I do not think you will hit your $70k target unless you get an assist by appreciation.   

What are my landlord options? 

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.

Be thankful for that, handle these challenges now, and remember why you are doing it.One day you will look back and be glad you powered through it. 

House hacking isn't an option for me, unfortunately, so the BRRRR method is what I'm considering. 

If you have a system like what i do you won't need an all in one a.i powered system.