Legally, can my landlord request that all rent payments be made out to her retirement fund?

Your landlord can request the way and manner that all rental payments are to be made out to concerning the premises that you occupy including that the payments be made out to her retirement fund.

This request by the landlord seems fine in that in all likelihood the real property that you are occupying could very well be an asset under your landlord's retirement fund. If that is the fact, there is nothing wrong that your landlord is doing concerning her request.

Good question.

There are two different issues here:

1) Can a landlord require payments be made out to her retirement fund? Yes, if either the lease you signed/agreed to states that payments should be made to the fund, or the lease gives the landlord the right to designate where/to what or whom to make the payments. (On the other hand, if the lease states to make payments to be payable to the landlord or her LLC, etc., then that's who you'd make the payments to--follow what the lease says.)

2) Is it possible the landlord is trying to get around her tax obligations? Yes--but that's not your  concern. You are not the authorities, and it's not your job to police what she does or what she reports. It's like if a contractor asks you pay him in cash, not by check--it's likely he's planning on underreporting taxes, but that's his concern (and crime, if he does it), not yours.

Make sure you keep records of all checks, so you can prove payment of your rent, even if they are not made out to the landlord per se. Get something in writing, including by emaill, from the landlord instructing you how to make out the checks. You will then be covered; what the landlord then does is not your problem, as long as  you can show payment in accordance with instructions. You may assume  the landlord is handling everything correctly, and are not required to assume otherwise.