Ideally I have skin in all three options for buying and holding as well as BRRRR down the road (diversifying).

Choosing the right location is the most important, as well as understanding its risk/return profile and decide if you're ok with it.

They have run STR in Cleveland for years and know the area very well!

I'm looking into this as well.

@Ryan DaultonIt sounds like a conversation with your IRA plan provider is in order.Perhaps this will help. 

Quote from @Brenden Evans: I’m also an out of state investor as well… I own some rentals in Cleveland and Milwaukee.

I have a duplex where I rent out the garage and in my lease I state:“Tenant understands that Landlord doesnot provide any security alarm system or other security for the Premises.

Yes, that's how I look at it (but quarterly as well as annually since we have such a seasonal market, I like to look at same quarter over quarter).  

@Bob Gruenig Yes I agree with @Chris Tracy that you should be talking to an SEC attorney. https://www.crowdfundinglawyers.net/ or https://syndicationattorneys.com/*You will need a real estate attorney as well but these people above will help guide you better.

For flood zones you can check flood maps – e.g. https://maps.austintexas.gov/FloodPro/ - if you work with a realtor, they should be providing you all that info.