Weirdly, you may actually be able to get better terms and/or more LTV on the refinance if there is debt on the property as lenders have rules for max cash in hand (max proceeds you get at closing) for cash-out refinances.  

Im now starting to doubt wether or not Cleveland is actually a good market to invest in?

It was actually more of a townhouse (just zoned as a condo).

My question is: when wholesaling, after finding a great deal, do you need real proof of funds to the get the property under contact or is there a way to get it under contract, find a buyer and complete a double closing/assign the right to sell without actually having the cash for the property? 

@Emeka Okeke, the biggest thing is actually doing it.  

I, personally, would be stressed about all that cash out of pocket though and would sell for piece of mind.San Diego, CA 2021 Real Estate Market Appreciation & Housing Market Trends - NeighborhoodScout

Nicholas,The one piece of advice I would give is refinance the Condo before you start renting it out. 

I see you are located in Royal Oak, that is the area we've actually been looking at as I'll be based in Warren at the Arsenal. 

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The mechanics of the transaction were actually very involved and some of the most intricate and detailed of any transaction I've been a part of, however the results were worth the effort.