Typically an option to renew, is just that - a renewal of the original lease, not an entirely new one. 

FHA loans are a good option for duplexes, particularly if you have between $200k and $250k to spend.

You should absolutely look into dynamic pricing platforms like Beyond Pricing or Pricelabs.

Finding an older house to rehab in those markets would be a better option in my opinion.  

There are some great options out there right now for cash out refi's.

I don’t use Stessa’s rent payment platform).As far as reporting issues and hiring contractors, I don’t have a fancy method/platform.  

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. 

What are the best financing options for this?

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. 

There are safe financing choices for real estate ventures, including seller financing, hard money loans, private loans, government-backed loans, crowdfunding platforms, and traditional mortgages.