However you can still out perform other investment options with RE.  

Feel free to reach out if you'd like to chat more!

After 2 years of renting it out we tried selling it to make our money back at no profit but not selling at that price over the summer ($500k), we bought it at $380k and put in $100k of reno's. 

As long as you don't fear climate change impacts, Florida is probably fine and buys today will probably work out great over the decades.

I hope things work out well for you.

I'd like to get started but am not sure where to start as an out of state investor.

You could start there when it comes to finding out more about build quality and the types of materials used in the homes. 

(Approach - 2) - He says that if he is asked to pull permits, he is not responsible for any additional work that the inspector may throw (basically more money out of my pocket on the rehab costs).

Talk with your lender about this proposal...  1) Get a solid quote on the roof replacement and share it with your lender.    2) Put the funds in escrow with your bank for the sole purpose of replacing the roof.    3) Close on the property.    4) Install the roof.    5) Get reimbursed for roof expense out of escrow.Most banks are fine with something like this if they know their downside is covered.  

Connecting with other investors can lead to potential deals and partnerships.Use Real Estate Websites: Check out sites like Zillow, Realtor.com, and Redfin to find properties that are priced lower than usual or have been sitting on the market for a while.