If you want to be that complicated I think that you should definitely sit down with an attorney.You can hold properties as joint ventures where LLC 1 and LLC 2 can have both names on title.

It's not really that complicated to buy out of state.

That always creates complications when an investment doesn't go well.  2. 

When families are involved it complicates business decisions and that usually means less money in your pocket . 

Another thing that may complicate things is I take out all the loans In the name of the LLC so Its a loan to the BusIness...Thanks!

So if your STR is not subject to SE taxes, then an S-election buys you nothing except EXTRA complication and expense.  

In this case, I think you're looking at the loser properties (because all the winners were sold quickly and often for list or more) and trying to draw sweeping conclusions about the state of a very complicated market.

If it is, the lender will have to appraise it - and that's a level of complication that you don't need.  

Otherwise, more complicated models, like the previously suggested NPV, IRR, DCF, MIRR are better suited. 

Its gets complicated if a mortgage is on just one of you guys and you guys have a loss.