Without a buyer's agent we were able to out-negotiate five other offers.

This can be challenging because if the numbers work putting 3.5% down, certainly investors who can likely offer better terms will buy it since they will be putting 20%-30% down.

I did look at Guestys new offer - Guesty Lite and it looks pretty good at a competitive price.

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Appreciate any advise you all have to offer. 

The one's that I have spoken with normally offer free consultations but won't honor it in this case and are demanding payment up front before they can even confirm whether or not they can do it.

There may be some reasons why it's not and only a CPA, EA or Tax Attorney that understands your full picture will be able to offer good advice on that.The Mgmt company will be it's own complete and separate entity with no ownership over any of the other LLCs.You may choose to have an umbrella LLC over the LLCs that own the property, but that's not really necessary.Set up your bookkeeping for the mgmt company. 

Have you tried talking to your accountant to see if s/he offers it?

I'm open to any financial advice you may offer regarding our current situation.

Vilano is about STR, however, I am seeing properties offered for 6 and 12 months, and there is an activity on those listings.