First, you need to realize that a single member LLC is considered a "disregarded entity" by the Federal IRS. 

Just because many real estate investors have failed miserably due to a complete lack of knowledge and disregard for basic strategy doesn't mean that real estate investing is not worth the hassle.

The Land Trust(LT) is disregarded, just like a single member LLC. 

please disregard

The vacation rental we are selling is owned by a single member LLC that is treated as a disregarded entity on our taxes.   

If it is available than disregard.

I guarantee it will be a lot less headache than separating every property into its own LLC with separate books and bank accounts.From a tax perspective it wouldn't matter too much since I assume all of these LLCs would be single member an thus treated as disregarded entities, which means it would flow directly to your Schedule E.

(The calculus also changes if you are filing with a tax status other than disregarded entity. 

I thought it unique that if you bought a property off market they would say it’s not an arms length transaction and disregard the sales price.

That said, not registering the entity in Tennessee can result in fines, and, worse, if there is a lawsuit against the LLC, it may be disregarded in Tennessee for the lack of being registered there.