If you have a lot of cash (millions and millions), you can sometimes gamble by just buying and holding forever.

I'm sure there are 1-off examples of success, but that's not the norm.And this isn't to shoot down North Lawndale - there are opportunities to invest in the current market/conditions, but to expect gentrification is a huge gamble.

Hence, you're asking for gambling advice from someone on the internet. 

If you intend to pay it off soon and retain the property then it's a gamble if you should have it or not.  

Your gambling on an appraiser. 

Given it is harder to find deals that are worth pursing from an underwriting perspective, but we are not comfortable with gambling with our investor's capital with that uncertainty. 

Well, first off anyone who bids 1% is gambling on the fact that the owner will redeem the property and NOT go over 3 years.

I am form Southern CA and never heard of it.In all seriousness, the holiday months of the winter are typically slower times for real estate sales, however, in a flip, time is your enemy and holding a Property longer just to get through that time is typically not going to be prudent as the costs to hold vs the potential higher sale price come Spring is a huge gamble I would not be willing to take. 

I think someone buying a property that doesn't positively cash flow and is counting on appreciation is taking a gamble, but to each their own.

Since the owner gets any overage past the tax/legal bill, its a gamble.