Would I get denied because of the recent transfer or would the asset value alone be enough?

I think you could split after sale for a non-taxable event, the total basis transferred in would be split across the two "new" properties.Calling @Dave Foster to give his insights here, lots going on in this one.

They helped us contact the real estate board and got the old manager to transfer all security deposits and back rents over to them.

He posted a question, similar to yours, He said he had 180k in liquid cash and he was looking to buy some 8 unit property where his entire 180k in capital plus more for all the closing costs and interest reserve and transfer taxes and the whole nine it would be near 200k. 

When one of these LLCs wins, they simply transfer the certificate to the main HF holdings.

That being said I will admit that covering transfer taxes both times can hurt your bottom line.  

I don't see why you would want to go through the hassle and expense of transferring the property into an LLC after the purchase was already completed.

If you have a loan, you may wish to look into due-on-transfer clauses.

After speaking with a real estate attorney, they had recommended transferring ownership of the property from the land trust into an LLC and dissolving the land trust.

I want to start advising my buyers to use land trust transfers when we acquire properties that have underlying notes since we are seeing an increase in notes being called.