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.

By doing ground-up construction and optimizing the design What was the outcome?

I would like to understand what are some of the best ways to finance a multi-family property once the down payment is fulfilled; thus the extra cost associated with the property is needed to renovate for optimal rental status.

I suggest not writing off everything this year to better position yourself for 2021.It's either that or you find a lender who does no income verification type of loans but those start in the high 5s low 6% range, not optimal. 

We hope to have our first short term rental in 2022.We have been with the same accounting  firm for some time and don’t feel that they are being proactive enough in helping us optimize any tax savings strategies.

Trust a specialized Deal Finder for the perfect property, a proficient Property Manager for tenant matters and maintenance, an optimal Lender for financing, and a trusted Contractor for repairs or renovations.