We originally hoped to rent as a mid term rental in a smaller town with a hospital, but the market quickly became oversaturated for the small demand so we decided to shift to long term rentals on both sides.

I was originally looking at Indian rocks beach but have extended my search to Seminole (both zoned for STR).

It's very easy for those "prying eyes" to see your transfer from the original title to the LLC (in California?)

I have insurance either way, but he said it's still best to split them up, with each having their own LLC.My plan is to create a new LLC for each one:-123 MAIN ST, LLC-123 GREEN ST, LLC...and then use my original LLC as the "Holdings Company", which then owns those 2 LLC's, and any additional properties I acquire.As of now, I have 1 business credit card and 1 business account for *JOHN SMITH PROPERTY INVESTMENT, LLC* -- this makes things easy from a bookkeeping standpoint.

If so does the cash out reset the loan to the original amount or does it increase it to include the value of the new unit (i.e. original loan was 300k and after cash out it becomes 550k?)

Originally listed for $149k.

Searched four sites and came up with a different decision than your original decision to go with them. 

Has new flooring and appliances but kitchen and baths are original but well maintained in above average condition.

It’s been unable to sell because the original house was a single wide in the 70s that was then added on to.This makes financing either difficult or very expensive for people (especially since it’s a low price point and mainly first time buyers).We would be paying cash - so it’s not an issue for us.

It was owned by the state highway department and was originally bought to put in a limited access highway interchange.