From what you mentioned here, it seems your motivations are reasonable.

Florida is the #1 net positive migration state in the country and, although there is little inventory right now, the supply/demand balance seems to be balanced right now.

You seem like someone with the same mindset, and drive that would be a good partner to achieve a common goal. 

Combining Houston's pleasant winters with Chicago's gorgeous summers seems like a winning combo!

There are not a ton of rental properties in the area but the price seems decently competitive based on the few other townhomes I see on realtor.com The photos in his listing are not great. 

But they are asking for whopping $1800 which seems insane.

They are existing STR and it seems that the house with the pool was preferred.

Seems many PMCs deliberately don't want to give too many details to owners about maintenance.1) You should be getting bids with supporting pics/videos for your approval.

I listen to Pace and he seems to really be sharp on Subject To (creative financing.)

This innovative approach seems promising, allowing buyers like me to acquire properties without the need for new financing upfront.However, as I navigate this journey, I'm also curious about how the compensation for real estate agents works within the context of a Subto deal.