Florida considers it to be a sale when it’s between separate legal entities; they deemed the sale to be in the price of the mortgage amount.

I'm bit stuck trying to figure out the legal ways to go about doing this as I am Canadian and am looking to invest in American markets.

Does the return now (rental income, asset appreciation, etc) outweigh the potential for rates to slightly drop in the unknown future?

He was charged around $4k for legal fees to remove the tenants, and $900.00 for each eviction and removal by the property manager.

So there really isn't a right or wrong path to take.And you'd also have to put yourself in the shoes of a potential acquiring company.  

So when I'm researching a property, if the last deed date was before 2000 then I know I have the potential of equity.

Yes there are quite a few around 350k, with lesser rent potential

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And that's not a sarcastic question, possible answers include but are not limited to...If management/ownership has been lazy and there's a lot of vacancy or below market units, that you can rent out and/or bring up to current market, then maybe you offer a little bit more for that upside potential. 

as a wholesaler after assigning contract to end buyer with existing mortgage and they take over, would it be reccomeded if i tell the end buyer about creative financing to another potential buyer