Since we don’t know what condition the house was in prior to her moving in, we only specified all the areas requiring cleaning and some large nails/screws in the walls, which she signed.

I am thinking instead of making the tenant sign all of the paper with new LLC for next three months, I should make her sign an addendum that states - She acknowledges that original lease was signed with KY LLC ( of course we will insert the real LLC name) and now the property is under new LLC.. so nothing changes,  all contracts , obligation stays the same as with the old LLC.Two questions:1.

Add a short statement at the end outlining whatever you are changing, have all parties date and sign, and you are done.Example: "Landlord and Tenant agree to extend this lease for an additional 12 months with a new termination date of 12/31/2025 and a new rent rate of $1,950.00 per month."

Fast forward to end of Jan 2024, we find a new set of tenants who sign a 1 year lease but break the lease in May due to a family emergency.

Your offer to purchase should include a requirement that the Seller provide all documentation and agree to sign an estoppel certificate (also called an estoppel form or agreement).

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

But I hear you, I know what I signed up for when I decided to be a landlord

I don't think managing your own properties will count because they will most certainly need that form signed off by an employer to verify the years and hours worked. 

All of them financial, with dollar signs in front. 

The seller who signed these leases would typically handle, and if it is not completed, then the lease is not official, as there are still contingencies for lessee to cancel if TI is not completed, presumably.3: Why are you paying any of the agent commission?