It sounds like you're at a crossroads between two strategies—both of which have valid points.

Then plan and design how you're going to deploy that cash via what strategy your wife and you have confidence in.I use a excel or google doc and my first sheet would layout all of the details of the sale including all costs that go into getting closed.

I got into RE investing utilizing the same strategy as you're exploring.

What strategy are you currently interested in pursuing?

. :)Anyway, I like your strategy of driving and looking for houses in need of repair and sending handwritten letters and contacting rentals for the reasons you gave.

2.What are the best and most cost-effective solutions for managing this potential long-term issue?

This doesn't seem like a good marketing strategy to me though. 

My family actually have some properties in FL, and I have also researched this area quite a bit and I saw it might fit my strategies. 

If you hate the process of placing tenants, it may be worth it to hire a property manager to handle tenant placement for you.I think finding a new tenant is a better long term strategy if you're confident you can find a higher quality tenant that will cause you fewer headaches.

There are so many strategies you can deploy depending on your goals going forward.