It would be void and regardless of recordation, no transfer or subdivision would have occurred.
But a new avenue has occurred to me that actually saves money on deed costs - nothing prevents multiple corporate entities from jointly owning a piece of real estate on one deed, right? So you could conceivably create one Delaware Series LLC, create an unlimited number of distinct legal entities with that, and then write one deed that lists all of those entities as joint owners of the single piece of real estate. Basically similar to multiple residents living in one house, and each getting a vote (but applied to infinitely scalable corporate entities!)
The fundamental flaw here is the law framing the entity itself as having voting rights (also why this attracts so much attention!), whereas if it were framed such that every beneficial owner with over say 35% of the ownership interest could vote, that would be intrinsically limiting.
Why would thirty companies that owned a company together get one vote each instead of one thirtieth? The thirty companies would each have one vote in determining how to vote the one parent's vote.
(You are, however, correct to note that you can record absolute gibberish if you want to, so long as you pay the recorder. This does not effectuate a transfer of land, though; it merely serves as constructive notice to the person who is bound to look for such recorded notice, i.e., the beneficial purchaser for value. In a way, you could think of the function of a recorder as preventer of race conditions, not the database).
Why would thirty companies each get a vote? Because that is what the charter says. There wouldn't be one parent company, rather the real estate would be owned by them all directly as tenants in common.
> 9. A. (2) Non-residents. Every property owner as of March 1 prior to the annual municipal election, whether a natural person or artificial entity, including but not limited to corporations, partnerships, trusts, and limited liability companies, and who is registered to vote, if provided by ordinance, shall have one (1) vote. A natural person shall be a citizen of the United States and age 18 on or before the date of the election. An artificial entity shall be a domestic entity in the State of Delaware.
https://charters.delaware.gov/fenwickisland.html
So they must be Delaware entities. Another thing I'm giving up on is that the Series LLC might not work. While each Series is legally independent from the others, I think they still might not be considered distinct "entities" (once again, not looking to give myself a headache to solidly determine that).
So either do one LLC/corporation per vote, or perhaps trusts might be even cheaper (no idea what filing/recording would be required for trusts, especially to substantiate them enough to register to vote)