I thought a cost segregation was a single study, not a continuum.  

So, we are segregating off our rental endeavors to a single LLC to protect our other operations. 

Some wholesalers may work with sellers for months or even years before a contract is ever signed.2.

But I don’t even play a lawyer on TV or the internet. 

If you run the numbers you will make far more money with 4 than the one you currently hold - even financed.  

Even when we do walk throughs on our turnovers before tenants leave, we often find a place looks like it will be fine on the initial walk-through and looks like a wreck once everything is gone. 

Even if only by $1.

And a single business. 

Still a Wolverine fan even though I've been in Fl for 20+ years.

Tax benefits can help make a better business deal, but a bad business deal is hardly ever going to break even just because of tax benefits.The other big consideration you should have, in order to actually benefit from real estate fueled losses or credits, it will require a substantial investment of time - either to get over the material participation thresholds for short term rentals, or to get over the real estate professional thresholds for mid term /  traditional rentals.