Out of over 40 owners, you are the one and only I have lost. 

Their credit scores are both over 700.

I don't want to spend hours on hours of listening to podcasts, picking up nuggets...and lots of fluff.  

Stop hanging out with your deadbeat buddies that spend all day drinking, talking sports, and otherwise wasting away.

One thing that Cape Coral does offer over the others though is that being a much larger market, inventory will be more diverse, so you might have better luck finding a specific property type and price point.

You will be very disappointed when you see your new hardwood floors all scratched up after spending countless hours refinishing them.

No you're definitely not paranoid or over thinking, please br careful 

You should always have a tenant as you're not only serving the 55 and over community (which will continue to grow), but the lower income demographic as well, which is needed.

I am a firm believer that the value of real estate will continue to increase year over year.

Each new property or business increases their (and your) risk exposure.The LLC helps a catastrophic loss from bleeding over into your other properties.