Am I missing anything significant in this thought process? 

I missed the cutoff for canceling my subscription by 8 hours and they wouldn't refund me the $369 they charged even though I don't want to use it anymore.

@Bayo Badejo, there are so many missing pieces here to even begin to give a real answer.What insights are you wanting?  

She missed other emails from the insurance provider confirming the policy did in fact cover all hazards.

Anything past that might feel weird.Good job going to your first one, that is a great step that too many people miss out on.

Airbnb properties can be hit or miss depending on location, seasonality, and regulations.

There should have been but this was missed in the rush of holidays and high traffic.

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

A young population plus a growing industry makes for good long term investments, but unless you are really scaling the cashflow can be hit or miss. 

For your $240K new-build townhouse, a cost seg may make sense if the tax savings outweigh the study cost (~$3K–$6K), especially since you plan to hold it for 10+ years and can benefit from immediate bonus depreciation.For the $380K older townhouse, cost seg with look-back depreciation could provide significant one-time deductions for missed depreciation over the past six years.