If so, they can sell within 2 years and not pay capital gains taxes on the sell of the home.They could take that money and buy multiple rental homes in other areas if they wanted, or use the money to downsize in to a different home while still having money left over.

Hello Solomon,A few tips I have for you would be to first; Analyze Deals Properly – Use the 1% rule (monthly rent ≥ 1% of purchase price) and calculate cap rate, cash flow, and ROI before buying. 

I am under contract to buy and flip a house that I am paying $615K for. 

.: So in 25 years people that buy now will be glad.

I have found that Redfin actually has pretty good search parameters to where you can look for listings that have been sitting a while that fit your buy box, and you can even do keyword searches for things like "as is", "investor", "seller financing", "guest house", etc. depending on what you are looking for.

As a CFA you probably know the old quote from Warren Buffett who said something like "buy what you know and understand". 

I wouldn't care who buys my property, I want to net the most amount of money in the shortest amount of time.

Even if one of you find insurance that you think covers your interest, it might be easier to buy, than cover a claim.You also run the risk of due on sale clause, because you are potentially notifying your lender in the transfer of ownership.Now I know nothing about insurance, so I could be totally wrong, but that's what I hear a lot of the nay-sayers say.

My goal for this deal is to purchase a cash-flowing multi family property to buy and hold.

Eventually, Class A property values increased to the point that even increasing rents didn't allow them to cashflow upon purchase.So, the flood of new investors switched to buying Class B properties.