Is the lawyer just being extra, extra careful...or are there typical scenarios where having it registered in NV will help for a property located in CA? 

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Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

My sister and I are not opposed to some sort of buy in as well, as it would likely help my father clear up some debts, and would just be nice to help him realize some sort of lump sum gain, in addition to what would likely be a share of monthly rental income.We are looking at setting up a trust to accomplish all of this, but are just at the beginning of this journey. 

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I'd be happy to help you in regards of that if you're still investing in central florida

How can I help? 

I want to say he was from Louisville, KY but no amount of searching is helping me...

My father would be willing to help us out in basically any way that he could, in exchange for modest monthly payments going forward, and is content limiting his capital gains exposure with the owner financing.