Flipping is really speculation subsidized by a deeply discounted purchase or creative financing justified by the sale, with renting as the most likely plan B to break even monthly at the least. 

Buying in an up and coming area in hopes that prices will go up is speculation. 

Attorney is placing a Phase 1 ESA approval contingency into our offer.Let’s speculate for a moment that the property passes either Phase 1 or Phase 2 ESA and we purchase. 15-20 years down the road we're ready to sell. 

Are you speculating and investing for appreciation...or looking for stability...what types of assets are you after...and you're leveraging bank money...$50k isn't going to get you very far...you're going to land on a Midwest metro area with limited funds...and the only right answer is what you are most comfortable with...all the major Midwest cities are going to have some similar characteristics...and all of them will have deals. 

I was also interested in Burlington City based on analysis (CoCROI, 2% Rule, 50% Rule etc....) and the revitalization efforts, which I guess is all speculative.  

If the last 12 month appreciation repeats itself into 2014, we will back to July 2007 prices right before the crash.Once we get back to July 2007 levels, I think market will start to become very speculative like Las Vegas and Phoenix where money will start pouring in even though properties do not cash flow.

Personally I think they should of allowed AIG to fail and let the insurers who weren't speculating the ability to pick up their assets for pennies.

But it all depends on how rigorous you are in estimating your expenses (and I suggest to err on the side of being more rigorous, than "flexible") and your investing criteria (maybe you are ok with large down payments, or with getting only 5% C/C ROI, or barely breaking even on cash flow since you are counting on appreciation/speculation).

If you are looking for speculative appreciation, the larger cities are good possible investments, however, the prices have already risen significantly so it is very hard to find good deals.Smaller towns and cities that haven't yet returned to their 2008 prices are where I recommend people to invest.

That may or may not be ideal for you (on the positive side, it is a locked in rate of return, instead of a speculative or hypothetical one).