If all are reasonable within the same timeframe (i.e a week or so) this is usually an indication the second was part of the purchase of the property.Obviously, you can ask the seller's but I generally find they do not know either which is why ask them to look at the closing documents so i know for sure.If the second is a non-purchase money loan like an HELOC for instance, then they will likely contend with the deficiency both as a foreclosure and short sale.

You'll also have to contend with their rules and regulations, the main one being the primary residence rule.  

The house would need to "fit in" pretty well.It is a good enough deal where I have a fairly hefty rehab budget, which is why I'm considering this.Also, at a certain point, can it be cheaper to rebuild completely than try to contend with a remodel on a dilapidated house?

Today some people contend it still does, and others say it is no longer the case.And remember you can do everything 100% legally with the best intentions, and that does not insulate you from a fair housing complaint.Also here is a great little article from the NAR.

Also, how do you contend with what seems to be a very high crime rate?

Regarding the last 20-30 points, I'd contend the last 20-30 points are difficult.

From responses on this thread, it seems Fredericksburg is a big contender for Cash Flow and Appreciation. 

@Mike McKinzie, @Adam WillisI've long contended one of the biggest problems with property management company's is their interests, as reflected in their fee structures, are not aligned with interests of the owner, or the customer (tenant).After interviewing most of the PMs in our areas of operations, we have concluded it will be necessary to develop our own capacity in-house as our holdings grow.  

If this is the case, your bordering on a few different neighborhoods which all carry varying unique factors to contend with.

The nay-sayers will say 'don't subsidize your losers' but others contend 'it's portfolio logic'.