I'm looking to combine attending a diverse educational event with a vacation somewhere in the US. 

Make sure there's several and that there's diversity.

I was sympathetic to their plight around Christmas, and that they are not originally from a western culture.

Before you message me asking why I chose them, it’s mainly for me the price of entry, amount of renters, good purchase price to rent ratio, and diverse economy.

If you genuinely feel bad then take money out of your own pocket and give it to them as charity but lets not further perpetuate the culture of entitlement that pervades much of this country. 

I look at it as diversity in my portfolio. 

I'm not sure how much the system itself is to blame vs. our own cultural expectations and ways of interacting with it (in general - not specific to AirBNB).  

I am extremely proud of our diverse and substantial multi-cultural employee and subcontractor base of staff.

I am excited for you, Central Florida is such a great diverse market

It's not speculation - it's a shortage of land (and thus housing) in an area that is desirable to live due to weather, culture, etc. with a highly skilled and well-paid workforce.