@Cole Payton, I’m of the mindset to go with conventional mortgages for houses that I plan on holding, until the reserve requirements become too difficult.  

Assuming she's on a month to month and your local laws only require 30 days' notice, you have two options.  1) Give her notice and tell her if she finds something sooner (eg June 1) and wants to move before that, you're okay with it. 2) refuse payment for the rest of May's rent as she's already late and start with the eviction.  

Both FNMA and FHLMC permit this, under the following circumstances: Notes: For all such transfers affecting mortgage loans purchased or securitized by Fannie Mae on or after June 1, 2016, the transferee is not required to occupy the propertya limited liability company (LLC), provided thatthe mortgage loan was purchased or securitized by Fannie Mae on or after June 1, 2016, andthe LLC is controlled by the original borrower or the original borrower owns a majority interest in the LLC, and if the transfer results in a permitted change of occupancy type to an investment property, such change does not violate the security instrument (for example, the 12 month occupancy requirement for a principal residence).The servicer must notify the borrower that a property transferred to an LLC must be transferred back to a natural person prior to any subsequent refinance application in order to meet Fannie Mae’s Selling Guide underwriting requirements.Citation: D1-4.1-02: Allowable Exemptions Due to the Type of Transfer (04/13/2022)Now, you will still have the Note and reporting in your name individually and will still be personally responsible for the mortgage and most likely, the manner of transfer will enable any litigant to pierce the veil of your LLC, but you'll have what you wanted, for whatever reason. 

- Recommendations for maintenance/cleaning services?

You dont need housekeepers or a 24/7 front desk staff, just a leasing agent and good maintenance staff. 

(He has them manage the units, but it is not required.)2.  

Auctions require advertising $.

Since you own the LLC / Land Trust, provided the activities you performed to earn material participation hours meet IRS requirements and the STR meets IRS requirements, then you should be able to offset non-passive income (W-2, 1099, etc.) with losses from this STR. ...

I have been approved for an SBA loan that would only require 10% equity and potentially less if i can get the seller to hold a note.

The leases require deposits and the renters know they are responsible for damages.