Learning how to structure FL rental property with land trust and LLC and confused

[Dave Allen]

Hello, brand new here on BiggerPockets. Learning a ton of info doing research about turning our 20 plus year primary residence into a rental property. At first I learned "use an LLC," no brainer, then I started learning more and now it's not a no brainer. Here is the situation:

We will be turning our 20 year homesteaded home in FL into a rental property when we move to Illinois. We will lose the homestead and that will cause a re-assesment and explode our property tax, but it is what it is. What I think I have learned in my research is this: It is best to put our property into a land trust, for asset protection (land trusts have one way asset protection in FL) and anonymity. The trustee will be a LLC we create in WY to hold the land trust for the anonymity and added asset protection.

The question I have run into now is that some things I am reading say that I will have to register the LLC in the state I live in, (will be Illinois) so I will be basically paying for two LLCs. 1. Is this true? 2. Seeing the situation, is my plan the best way to move foreward or does anyone have a better way?

Thank you, :) 

[John O'Leary]

Call RTR title. Hope (the attorney) does a lot of these for FL investors. She's located in Orlando.