Tenant-occupied listings sell at a discount and sit longer, and the management record is usually why

The analysis here is solid, and the sequencing point is the one that actually matters. Most of the friction you are describing is created in the ninety days before listing, when the owner thinks they are just getting the property ready rather than preparing a business record for buyer review.

On the financial records piece, the assumption doing the most work is that buyers and their attorneys treat a residential rental like a residential purchase. Many do not. Once a tenant is in place and rent rolls are part of the story, the diligence lens shifts closer to commercial practice, and a partial waiver with no written rationale or an unapproved maintenance charge becomes a signal about the whole record, not an isolated line item. Clean the ledger before the listing goes live, or you will be explaining it under time pressure during the inspection period, which is the worst possible position.

The evergreen clause risk is the one most owners miss entirely. A management agreement that auto-renews or has a tail on termination can survive a sale unless it is explicitly addressed in the purchase contract and the management termination is documented before closing. That is a contract law question, so a real estate attorney needs to review the specific agreement language, not a general observation about what leases usually say.

On tenant cooperation, the rent credit approach works, but the amount and structure matter. Too small and the tenant sees it as transactional and ignores it. Too large relative to the remaining lease term and the buyer starts asking why the seller needed to pay for access to their own property. The right number is whatever reflects a genuinely maintained relationship, which is the point, managing the relationship before the exit matters as much as managing it during tenancy.

What is the remaining term on the management agreement relative to the lease, and does the termination clause require notice from the owner or is it triggered automatically by a sale event?

The checklist a careful operator runs before listing: confirm the security deposit is held in the correct account with a paper trail the buyer can verify, audit every waived or reduced charge for a signed addendum, and pull the management agreement to find the termination clause and any evergreen provision so you can cure or disclose it before the purchase agreement is drafted.

The piece I would add to the lease assignment question is estoppel. A tenant estoppel letter, signed before listing, locks in the tenant's acknowledgment of the current rent, the lease term, and any claims they intend to assert. Without it, a buyer's lender or attorney will often require one at closing anyway, and getting a reluctant tenant to cooperate at that stage is far harder than getting them to sign at the start of a transaction where the owner still controls the relationship.

Does the lease include any option to purchase, right of first refusal, or renewal language the buyer would inherit, because that changes the assignment analysis considerably?

The Albuquerque fourplex I lost mid-contract died exactly on the security deposit ambiguity point.