They will more than pay for livelihood, allowing me to speculate a bit, leverage other properties,  etc.  

No need to speculate how the conversation went and add fuel to the fire of this thread.

I went from being seen as the ignored speculative neighbor that gives the HOA a hard time to everyone wanting me on the board. 

., taking the speculation out of your question about the what-ifs, in my case the refi will take all the investors out of the deal.

What would be the harm of comparing past performance and THEN making a decision if one will perform better or worse in the future, you know, SPECULATING?

Do no speculate in real estate and hope for prices to go up.

One caution is a property that size will have a limited market since it won't be able to get residential financing.The quadraplexes look to me like a pure appreciation/speculation play - I wouldn't want to be highly leveraged on those. 

ThanksGreg You didn't specify the upside nor speak of a value add play in the deal so it's a little difficult to speculate how to best structure a creative financing package.Assuming it's a value add play with good risk adjusted gains at the end of the process then maybe the safest route is to negotiate a wrap transaction with the seller, and if your are concerned about a due on sale clause make it contingent on the lenders approval.The seller will confront these same financing scenario issues with all other buyers so if they want to sell the property then they can either deal with the issue with a reset and able buyer, you, or kick the can down the line looking for another buyer who maybe willing to assume a less than stellar financing package.As the buyer though your only concern should be the financing package that delivers you title, assuming you plan on making extensive improvements to the property, and allows you to earn what you determine is a reasonable cash flow from the project.Options aren't bankable.

However, how do you ensure you are staying on the side of "investing" rather than "speculating?" 

@Brooke Ray - what you are proposing is very speculative.