This depends on how the deal is structured and what rights and responsibilities you retain vs what you transfer to your current tenant.

I have a few rentals on the lower end of the spectrum that to me, have more of a liability issue. Right now, they are under my main LLC with a lot of my more high end property. Would it be worth it to create a new LLC...

I'm curious to try them out for at least one owner occupied client transaction to see how they work at transferring the loan, forms they file, required contract wording, etc. 

There was a change recently, a few years ago now at least, where transfer to Title to a LLC of your own is okay. 

The transfer of title could trigger negative covenants in the loan (eg: Due on Sale Clause).

Hello everyone, I am looking for advice on the best way for my mother to transfer the property to my name.

However, a loan officer suggested getting a vacation home loan, then transferring the property to an LLC.

Also, for the second part of the strategy, we would transfer the duplex into our real estate property investment LLC after year 1 and have my sister move back into the single-family house as her primary and rent out both units in the duplex as short/mid-term rentals.

This would be the beginning of the brrrr method and I would have 3 rentals right away.My questions are 1. is it better to start an LLC for RE and transfer my existing property into the LLC? 

That permits you to easily transfer the bills if the unit becomes vacant and monitor that each tenant is actually paying the bills and keeping the property in working order so to speak.