@Jesse SteinI am betting that you don't want to pay much for the guy who collects rent and checks on things.

I agree the virtual real estate seems like quite the gamble, especially when there are viable real world options that would be a much safer long term bet.

Your best bet would likely be to get a hard money loan for purchase.

I bet there you will find 100% wholesalers.

This is a bank that works with a lot of investors, so they were my best bet.  

If you can keep labor prices down, I’d say it’s a pretty safe bet— given the right area.

If you're lucky and the attic is brutally hot, the ducts will have a harder time cooling the air down enough, so you'll have less condensation than in your "well ventilated" crawlspace, but that's still not a good bet to take.It is one thing to see regular joe schmoes not understand this, but it is absolutely infuriating to see that inspector gave literally the opposite of the correct diagnoses.You can choose to waste obscene amounts of money moving all your ductwork. 

I'm not betting on appreciation, but based off of recent sales, I've definitely seen buyers pay more than the sellers did a few years ago.

You can yell scream and rant all you like... proof is all around you, and I bet the thousands of investors reading this post read this and think...

Here's my opinion regarding the South Shore- Purchasing a stabilized and cash flowing building is a good bet; but I don't believe you will see very much appreciation due to the Obama Presidential Centre.