I have used online loan calculators and been researching for properties and it has not left me with much optimism.

Which is a bad idea, frankly, because depreciation has multiple options, and no software can do optimization for you.

There’s a platform called PadSplit to help you optimize the host experience. 

Domain specific CPAs' are typically would be in this category with deeper understanding of rules and would be able to help clients with optimizations etc such as @Brandon Hall .

How do you optimize your pricing to attract more guests without compromising profitability?

I possibly would let these ride indefinitely as I have rentals to offset these, but the wife probably will want to use the resource/units to optimize profit and it is unclear that the STR/MTR option is optimal on 3 of the units.  

Transferring money to the individual buying the property instead of contributing it to the LLC gives you no basis in the LLC, which can cause multiple problems.Agree with other pros that an S Corp is generally not going to be optimal here based on the face value of the facts.I assume there is a reason you're attempting to structure it like this...perhaps to obtain more advantageous financing.

It's never going to be the absolute optimal time to purchase.

The boiler plate ones that are provided by online services are very generic and are not optimized for the goal of your LLC.

Investors seeking to optimize their assets, defer taxes on large capital gains, and secure their financial future often explore various trust structures to achieve their objectives.