I do not intend on transferring the property ownership to the LLC, however, wanted to get you guys’ input on whether an LLC is beneficial for business operations (i.e. bank account for income and expense, direct deposit for rent from house hacking, etc.)?

When I started, I gave tenants my bank account number and told them they had to deposit or transfer the money into that account by the due date in the lease. 

Would you suggest I still look at more expensive options or is it easy to transfer the site over later if I do decide to do more with it?

Would the transfer of property be considered at the end of 5 years when the option is exercised?

For example, I was hoping to write off the cost of the LLC formation, wire transfers, and advisory fees.

The only way we could find financing on this small of an amount was through a mortgage broker who then transferred the loan to another lender (Wells Fargo).

Are you buying it individually then finding a lender who will transfer the mortgage to your LLC?

I just need permission to transfer back to a land trust after closing.

Just sounds like planning for a lot of cash transfers to me.You don't report them separately on your taxes, and there's plenty of budgeting/tracking software to keep the per-property data separate.

You need the money in a checking account in prior months sitting there you cannot have recently transferred funds without a trail or history (Patriot Act).